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CAS No. : | 1931-63-1 | MDL No. : | MFCD09031979 |
Formula : | C10H18O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JMLYDLZRFNYHHO-UHFFFAOYSA-N |
M.W : | 186.25 | Pubchem ID : | 74732 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 100% 2: 100% | Stage #1: Methyl oleate With ozone In dichloromethane at -78℃; Stage #2: With triphenylphosphine In dichloromethane at -78 - 23℃; for 18h; | 4 A solution of methyl oleate ( 10.0 g, 33.7 mmol) in anhydrous CH2Cl2 ( 100 mL) was cooled to -78 °C and a stream of O3 was bubbled through the reaction mixture until the solution became lightly blue ( 10 min). Argon was bubbled through the mixture and a solution of PPh3 (19.7 g, 75.1 mmol) in CH2Cl2 (100 mL) was added slowly. The reaction mixture was warmed to 23 0C and stirred for 18 hours. The solvent was evaporated to dryness and the solid was triturated with cold hexane (80 mL). The EPO filtrated was evaporated to give a yellow oil. The oil was purified by chromatography on silica gel (CH2Cl2:Hex, 1 : 1 and then CH2Cl2:Et2θ, 1 : 1) to provide the two expected aldehydes, nonanal (4.80 g, 100%) and methyl 8-formyloctanoate 12 (6.28 g, 100%), both as colourless oils. 1H NMR (300 MHz, CDCl3) δ 9.76 (s, IH), 3.66 (s, 3H), 2.41 (t, J= 7.3 Hz, 2H), 2.30 (t, J= 7.3 Hz, 2H), 1.61 (m, 4H), 1.31 (m, 6H). 13C NMR (75 MHz, CDCl3) δ 202.4, 173.8, 51.1 , 43.5, 33.7, 28.7, 28.6, 28.5, 24.5, 21.7. MS (APCI): 187 (M+ l)+. Rf= 0.2 (CH2Cl2). |
1: 96% 2: 74% | With N-methyl-2-indolinone; ozone at 0℃; | |
75% | Stage #1: Methyl oleate With ozone In methanol; dichloromethane at -78℃; Inert atmosphere; Stage #2: With acetic acid; zinc In methanol; dichloromethane for 0.5h; Inert atmosphere; |
With ozone; acetic acid; zinc 1.) MeOH, CH2Cl2, -78 deg C, 2.) MeOH, CH2Cl2, 30 min; Multistep reaction. Yields of byproduct given; | ||
With ozone at 200℃; for 0.0833333h; | ||
With ozone In hexane at -78℃; | ||
With ozone; acetic acid Behandlung der Reaktionsloesung mit Zinkstaub und Wasser; | ||
With ozone; acetic acid; zinc 1.) MeOH, CH2Cl2, -78 deg C, 2.) MeOH, CH2Cl2, 30 min; Yield given. Multistep reaction; | ||
With sodium tungstate; alkylated polyethyleneimine; dihydrogen peroxide at 22℃; for 24h; | ||
With sodium periodate; ruthenium In water; 1,2-dichloro-ethane at 20℃; for 12h; | ||
Stage #1: Methyl oleate With ozone In dichloromethane at -78℃; for 1h; Stage #2: With dimethylsulfide In dichloromethane at 25℃; for 6h; | 1 Example: 1Preparation of Hexadecyl cis-9-Tetradecenoate: Preparation of hexadecyl cis-9-tetradecenoate, 4 was carried out according to the Scheme 1. Oleic acid methyl ester, 1 (12.0 g, 0.0314 mol) in dichloromethane (100 ml) was cooled to -78 degree. C and ozone gas was bubbled into the reaction mixture for 1 hr. After reaction, the reaction was quenched by adding dimethyl sulphide (DMS, 8 ml) and was stirred for 6 hr at 25° C. The solvents were removed under vacuum and the residue 2 thus obtained (4.25 g, 0.022 mol) was used directly for the preparation of cis-9-myristoleate, 3. n-Pentyl-triphenyl phosphonium salt (11.16 g, 0.027 mol) was taken in 50 ml of dry THF and cooled to 0° C. To this slurry, n-butyl lithium (17.0 ml, 1.6 M in hexane) was added, stirred the reaction mixture for 0.5 hr to obtain an orange solution. 1-Al-methyl nonanoate containing crude product 2 (5.0 g, 0.027 mol) dissolved in dry THF (20 ml) was added to the above contents slowly and allowed the reaction mixture to reach to 25 degree. C and then heated to reflux temperature to reflux for 4 hr. The reaction was monitored by TLC and after completion of the reaction, THF was removed from the reaction mixture under reduced pressure, and to the residue distilled water 825 ml) was added and extracted with ether (25 ml×3 times). The combined ether layer was dried over anhydrous sodium sulphate and solvent was removed and dried under vacuum to get the residue and was purified by column chromatography using hexane and ethyl acetate (98:2) as eluent to get cis-9-myristoleate, 3 (4.2 g, 0.0175 mol) in 65% yield with 66% purity by GC. cis-9-Myristoleate, 3 (4.2 g, 0.0175 mol) was enzymatically transesterified with cetyl alcohol (5.08 g 0.021-mol) in the presence of Lipozyme TL IM (0.930 g, 10 wt % of the total substrate) at 68° C. for 8 hr. The reaction was monitored by TLC and after completion of the reaction, hexane (50 ml) was added and the lipase was separated by filtration and the solvent was evaporated to get the crude product and was purified by column chromatography to obtain hexadecyl cis-9-tetradecenoate, 4 (7.48 g, 0.0166 mol) in 95% yield with 92% purity by GC. The structure of hexadecyl cis-9-tetradecenoate, 4 was confirmed by 1H NMR, IR, and GC-MS.Spectral Data:1H NMR: (600 MHz, CDCl3): δ 5.36-5.33 (m, 2H, J=3 Hz, -CHCH-), 4.01 1.99 (m, 4H, -CH2-CHCH-CH2-), 1.60 (m, 4H, -CH2-CH2-CHCH-CH2-CH2-), 1.30-1.20 (br, d, 38H, -CH2-CH2-CH2-), 0.90 (q, 6H, -CH2-CH3).IR (neat/NaCl): 2926, 1738, 1654, 1242, 721 Cm-1.GC-MS: m/z: C30H5802 (M+): 450. | |
With ozone In water; propionic acid for 1h; | 1 Example 1Comparative ExampleOzonolysis and Oxidation without Addition of Acid20 g of a 0.182 molal solution of methyl oleate (95% pure) in a solvent mixture of propionic acid and water (15 equivalents based on moles of double bond) were initially charged in a two-neck flask with gas inlet tube and reflux condenser. The feed gas, consisting of 5% by volume of oxygen in carbon dioxide was passed through an ozone generator at a flow rate of 40 ml/min. The ozone generator was set to maximum power. The ozone-containing gas mixture was passed into the reaction mixture with stirring. The offgas stream was passed by means of gas wash bottles into a 5% aqueous potassium iodide solution. After 60 minutes, the substrate was converted, and the gas introduction was then stopped. According to GC analysis, the reaction mixture had a content of 39.5 wt % of 9-nonanal and 38.2 wt % of methyl 9-oxononanoate.After adding hydrogen peroxide (0.454 g of a 30% aqueous solution), the reaction mixture was then heated to 100° C. in an oil bath. After 120 minutes, nonanal and methyl 9-oxononanoate were converted completely to the respective carboxyl compounds. GC analysis: 41.05% pelargonic acid, 39.65% monomethyl azelate (FID signal, figure in area percent, uncorrected). | |
Multi-step reaction with 3 steps 1: [((S,S)-N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine)FeII(OTf)2]; dihydrogen peroxide / acetic acid; acetonitrile / 2.5 h / 0 °C 2: sulfuric acid / acetic acid; acetonitrile; water / 16 h / 20 °C 3: sodium periodate; sodium hydrogencarbonate / acetic acid; acetonitrile; water / 1.5 h / 20 °C | ||
With oxygen at 85℃; for 6h; | ||
Multi-step reaction with 3 steps 1: formic acid; dihydrogen peroxide / neat (no solvent) / 8 h / 20 - 30 °C / Cooling with ice 2: boron trifluoride diethyl etherate / dimethyl sulfoxide / 22 h / 80 °C / Inert atmosphere 3: N-methyl-4,5-dimethylthiazolium iodide; potassium carbonate / acetonitrile / 0.5 h / 130 °C / Microwave irradiation; Inert atmosphere | ||
With oxygen at 85℃; for 6h; | ||
With sodium periodate; C24H28ClN4O2Ru(1+)*F6P(1-) In dichloromethane; water; acetonitrile at 65℃; for 8h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: Methyl oleate With ozone In dichloromethane Stage #2: With dimethylsulfane In dichloromethane | |
96% | With oxygen; ozone; N-Methylmorpholine N-oxide In dichloromethane at 0℃; | |
93% | With oxygen; ozone; N-Methylmorpholine N-oxide In dichloromethane at -78 - 20℃; for 2.41667h; | Synthesis of methyl 9-oxononanoate 4-Methylmorpholine N-oxide monohydrate (5.9 g, 50.6mmol,3.0 equiv) was dehydrated by heating at 90 °C under high vacuum overnight. Following the ozonolysis conditions of Drussault [12], a 250mL round-bottom flask equipped with stir bar was charged with methyl oleate (5.0 g, 16.9 mmol, 1.0equiv), the anhydrous 4-methylmorpholine N-oxide monohydrate prepared above, and anhydrous DCM (100 mL). Stirring was initiated, affording a clear solution. The reaction mixture was cooled to -78 °C for 15min before bubbling in amixture of ozone/oxygen. Conversion was complete within 10 min. The ozone generator was turned off and oxygen was bubbled through the solution for additional 10 min. The reaction mixture was allowed to warm to room temperature and aged for 2 h. The reaction was concentrated and the residue was dissolved in ethyl acetate (200 mL) and washed with water (80 mL) and brine (50 mL), dried over sodium sulfate, filtered, and concentrated to give a yellow oil. The oil was purified by chromatography on silica gel (hexane:EtOAc2:1) to provide methyl 9-oxononanoate (2.9 g, 93% yield) as a colorless oil. The spectral data were same with the one in published literature [9, 10]. |
81% | Stage #1: Methyl oleate With ozone In methanol at -60℃; Stage #2: With dimethylsulfane In methanol at -60 - 20℃; for 4h; | |
64% | With oxygen In methanol at -65℃; for 3.5h; | |
57% | With 2,3-dimercapto-succinic acid; ozone In methanol 1.) -60 deg C, 2.) -10 deg C, 1 h, 3.) 0 deg C, 1.5 h, 4.) 20 deg C, 1 h; | |
43% | Stage #1: Methyl oleate With anhydrous sodium carbonate; ozone In methanol; dichloromethane at -78℃; Stage #2: With triethylamine In methanol; dichloromethane at 0 - 20℃; for 6h; | |
41% | Stage #1: Methyl oleate With ozone In methanol at -30℃; Stage #2: With acetic acid; zinc powder In methanol at 30℃; | |
33% | Stage #1: Methyl oleate With ozone In dichloromethane at -78℃; for 4.5h; Stage #2: With triphenylphosphine In dichloromethane at 20℃; for 13h; | |
(i) O3, CH2Cl2, (ii) Ph3P; Multistep reaction; | ||
With ozone; triphenylphosphine Yield given. Multistep reaction; | ||
With sodium dihydrosulfite; ozone 1) methanol, -78 deg C, 15 min, 2) room temperature, 30 min; Multistep reaction; | ||
With lead tetraacetate; osmium(VIII)-tetroxide; hydrogen; manganese(II) oxide 1.) acetone, 23 deg C, 8 h, 2.) CH2Cl2, -40 deg C, 0.5 h; Yield given. Multistep reaction; | ||
Stage #1: Methyl oleate With ozone In methanol; dichloromethane at -17℃; Stage #2: With dimethylsulfane In methanol; dichloromethane at -17℃; | ||
Multi-step reaction with 3 steps 1: formic acid; dihydrogen peroxide / 5 h / 60 °C 2: anhydrous phosphorous acid / water monomer / 3 h / 90 °C 3: sodium (meta)periodate / water monomer; acetonitrile; dichloromethane / 2 h / 20 °C | ||
Multi-step reaction with 4 steps 1: formic acid; dihydrogen peroxide / 5 h / 60 °C 2: anhydrous phosphorous acid / water monomer / 3 h / 90 °C 3: 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; acetic acid / methanol / 1.5 h / 50 °C 4: 3-butyl-4,5-dimethylthiazol-3-ium trifluoromethanesulfonate; potassium carbonate / 0.25 h / 180 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With Celite; pyridinium chlorochromate In dichloromethane at 20℃; for 3.5h; | |
90% | With Dess-Martin periodane In dichloromethane at 0℃; | 2 To a solution of methyl 9-hydroxy nonanoate (1g) in dichloromethane (8ml) at 0°C was added Dess- Martin periodinane (1.7 equiv; 3.83g). The ice bath was removed after 10 minutes, and the reaction was allowed to proceed for up to 2 hours (until no starting material remained by TLC). The reaction was diluted with 200ml of 10% ethyl acetate/hexane, and it was immediately poured onto silica gel. Elution with the same solvent produced the product aldehyde in 90% yield (890mg). |
87% | With pyridinium chlorochromate In dichloromethane at 20℃; for 3h; Inert atmosphere; Molecular sieve; |
83% | With Celite; pyridinium chlorochromate In dichloromethane at 20℃; for 4h; | |
81% | With 4 A molecular sieve; pyridinium chlorochromate In dichloromethane at 25℃; for 2.5h; | |
81% | With dipyridinium dichromate; Celite In dichloromethane at 20℃; for 4h; | |
80% | With Celite; pyridinium chlorochromate In dichloromethane at 24 - 26℃; for 2h; | |
71% | With pyridinium chlorochromate In dichloromethane | |
61% | With pyridinium chlorochromate In dichloromethane | |
60% | With pyridinium chlorochromate In dichloromethane for 4h; Inert atmosphere; | |
With pyridinium chlorochromate In dichloromethane | ||
With Celite; pyridinium chlorochromate In dichloromethane for 2h; Yield given; | ||
With oxalyl dichloride; dimethyl sulfoxide; triethylamine 1.) CH2Cl2, -78 deg C, 2 h, 2.) CH2Cl2, -78 deg C to room temp.; Yield given. Multistep reaction; | ||
With oxalyl dichloride; dimethyl sulfoxide; triethylamine | ||
With pyridinium chlorochromate In dichloromethane at 20℃; for 15h; | 11.2 Step 2; 9-Oxo-nonanoic acid methyl ester; To a solution of 5.2 g (28 mmol) 9-Hydroxy-nonanoic acid methyl ester in 350 mL DCM is added 9.1 g (41 mmol) Pyridinium chlorochromate and the reaction is stirred for 15 h at rt. The reaction is diluted with DCM, silica is added, the mixture is filtered through a pad of Hyflo and thoroughly washed with DCM. The solvent is removed in vacuo to give the title compound as a green oil, which is used without further purification. MS (method D): 204 [M+H2O] | |
35.3 g | With manganese(IV) oxide In ethyl acetate at 50℃; for 8h; | 1-6 Preparation of methyl 9-oxononanoate Methyl 9-hydroxydecanoate (37.6 g, 0.2 mol) and MnO2 (17.4 g, 0.2 mol) were placed in a reaction kettle, 200 ml of ethyl acetate was added, stirring was started, 180 rpm, temperature 50 ° C, real-time monitoring The reaction was carried out, and after 8 h, it was cooled to room temperature, filtered, and the solvent was evaporated under reduced pressure to give 35.3 g of white solid product |
With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane at 20℃; for 1h; Inert atmosphere; | Synthesis of compound 2: methyl dec-9-ynoate Methyl 9-hydroxynonanoate (10, 4.00 mmol, 0.753 g) was dissolved in CH2Cl2 (16 mL) and added NaHCO3 (8.00 mmol, 0.672 g, 2.00 equiv.) and Dess-Martin periodinane (4.80 mmol, 2.21 g, 1.30 equiv.). The mixture was stirred at room temperature for one hour under argon, and was then diluted with heptane (80 mL). The resulting mixture was filtered and the filtrate was then passed through a pad of silica gel (3 cm). The silica pad was rinsed with solvent (EtOAc:heptane, 1:4, 200 mL) and the filtrate evaporated in vacuo. The residue was dissolved in dry methanol (40.0 mL). K2CO3 (8.0 mmol, 1.10 g) was added and the system was flushed with argon before dimethyl(1-diazo-2-oxo propyl) phosphonate (4.40 mmol, 1.1 equiv., 10.0 mL 10% in MeCN) was added. After stirring for two hours at room temperature, the mixture was diluted with Et2O (100 mL) and transferred to a separatory funnel. A solution of 5% aq. NaHCO3 (50 mL) was added and the layers were separated. The aqueous layer was extracted with Et2O (1x30 mL) and the organic extracts were combined and washed successively with 5% aq. NaHCO3 (3x30 mL), brine (1x30 mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel (3-5% EtOAc in heptane) to afford the desired product 2 as a colorless oil in 57% yield (0.413 g) from 10. Rf=0.30 (EtOAc:heptane, 1:9. KMnO4-stain). 1H NMR (400 MHz, CDCl3) δ 3.62 (s, 3H), 2.26 (t, J = 7.5 Hz, 2H), 2.14 (td, J = 7.0, 2.6 Hz, 2H), 1.90 (t, J = 2.7 Hz, 1H), 1.65 - 1.53 (m, 2H), 1.53 - 1.43 (m, 2H), 1.32 (m, 6H). 13C NMR (101 MHz, CDCl3) δ 174.2, 84.6, 68.2, 51.5, 34.1, 29.0, 28.8, 28.6, 28.4, 24.9, 18.4. The spectroscopic data was in agreement with that reported in the literature | |
With pyridinium chlorochromate In dichloromethane at 20℃; for 1.41667h; Inert atmosphere; Cooling; | Preparation of 10 (methyl-9-oxo-nonanoate) 9(600 μl, 2.8 mmol) was added to a solution of PCC (900 mg, 4.2 mmol) in dry DCM (50 ml) under argon at -15° C., and the mixture was stirred for 45 min. Reaction progress was monitored by TLC. The reaction mixture was allowed to return to room temperature and was stirred for an additional 40 min. The mixture was then filtered over Celite, and the residue was washed with ether. The filtrate was concentrated in vacuo. Flash column chromatography on silica using a gradient of 0-100% ethyl acetate in hexanes afforded 10 at 70% purity (containing about 30% starting material) (305 mg, 1.64 mmol, 58% yield). 1H NMR (600 MHz, chloroform-d): δ (p.p.m.) 9.76 (t, 1.79 Hz, 1H), 3.66 (s, 3H), 2.42 (td, 7.30, 1.77 Hz, 2H), 2.30 (t, 7.60 Hz, 2H), 1.62 (m, 4H), 1.32 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example: 1Preparation of Hexadecyl cis-9-Tetradecenoate: Preparation of hexadecyl cis-9-tetradecenoate, 4 was carried out according to the Scheme 1. Oleic acid methyl ester, 1 (12.0 g, 0.0314 mol) in dichloromethane (100 ml) was cooled to -78 degree. C and ozone gas was bubbled into the reaction mixture for 1 hr. After reaction, the reaction was quenched by adding dimethyl sulphide (DMS, 8 ml) and was stirred for 6 hr at 25 C. The solvents were removed under vacuum and the residue 2 thus obtained (4.25 g, 0.022 mol) was used directly for the preparation of cis-9-myristoleate, 3. n-Pentyl-triphenyl phosphonium salt (11.16 g, 0.027 mol) was taken in 50 ml of dry THF and cooled to 0 C. To this slurry, n-butyl lithium (17.0 ml, 1.6 M in hexane) was added, stirred the reaction mixture for 0.5 hr to obtain an orange solution. 1-Al-methyl nonanoate containing crude product 2 (5.0 g, 0.027 mol) dissolved in dry THF (20 ml) was added to the above contents slowly and allowed the reaction mixture to reach to 25 degree. C and then heated to reflux temperature to reflux for 4 hr. The reaction was monitored by TLC and after completion of the reaction, THF was removed from the reaction mixture under reduced pressure, and to the residue distilled water 825 ml) was added and extracted with ether (25 ml×3 times). The combined ether layer was dried over anhydrous sodium sulphate and solvent was removed and dried under vacuum to get the residue and was purified by column chromatography using hexane and ethyl acetate (98:2) as eluent to get cis-9-myristoleate, 3 (4.2 g, 0.0175 mol) in 65% yield with 66% purity by GC. cis-9-Myristoleate, 3 (4.2 g, 0.0175 mol) was enzymatically transesterified with cetyl alcohol (5.08 g 0.021-mol) in the presence of Lipozyme TL IM (0.930 g, 10 wt % of the total substrate) at 68 C. for 8 hr. The reaction was monitored by TLC and after completion of the reaction, hexane (50 ml) was added and the lipase was separated by filtration and the solvent was evaporated to get the crude product and was purified by column chromatography to obtain hexadecyl cis-9-tetradecenoate, 4 (7.48 g, 0.0166 mol) in 95% yield with 92% purity by GC. The structure of hexadecyl cis-9-tetradecenoate, 4 was confirmed by 1H NMR, IR, and GC-MS.Spectral Data:1H NMR: (600 MHz, CDCl3): delta 5.36-5.33 (m, 2H, J=3 Hz, -CHCH-), 4.01 1.99 (m, 4H, -CH2-CHCH-CH2-), 1.60 (m, 4H, -CH2-CH2-CHCH-CH2-CH2-), 1.30-1.20 (br, d, 38H, -CH2-CH2-CH2-), 0.90 (q, 6H, -CH2-CH3).IR (neat/NaCl): 2926, 1738, 1654, 1242, 721 Cm-1.GC-MS: m/z: C30H5802 (M+): 450. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.52% | Stage #1: triphenylheptylphosphonium bromide With sodium amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 1.5h; Stage #2: methyl ester of azelaic acid aldehyde In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -73 - 20℃; | |
(i) K, HMPT, (ii) /BRN= 1766823/; Multistep reaction; | ||
With sodium amide 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT; Yield given. Multistep reaction; |
1.7 g | With potassium carbonate In toluene for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium tetrahydroborate In ethanol for 0.25h; | |
93% | With 5%-palladium/activated carbon; hydrogen In methanol at 50℃; for 4h; Inert atmosphere; | |
72% | With sodium tetrahydroborate In methanol at 20 - 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With sodium hexamethyldisilazane In tetrahydrofuran at -85℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphate buffer; α-oxidase of peas (Pisum sativum); oxygen; Triton X-100 at 4℃; for 23h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With air at 1130℃; Formation of xenobiotics; high pressure combustion; Further byproducts given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 37 percent / Ba(OH)2*8H2O / methanol 2: BH3*Me2S / tetrahydrofuran / Ambient temperature 3: PCC, Celite / CH2Cl2 / 2 h | ||
Multi-step reaction with 4 steps 1: 37 percent / Ba(OH)2*8H2O / methanol 2: Et3N / tetrahydrofuran / 0.5 h / -5 °C 3: NaBH4 / tetrahydrofuran; H2O / 1 h / Ambient temperature 4: PCC, Celite / CH2Cl2 / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diethyl ether 2: aq. KOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.9% | In methanol | (Method C) (Method C) A solution of methyl oleate (10.0 g) in methanol (100 ml) was purged of ozone with stirring at -20° C. for 1 hour. The reaction mixture, with dimethylsulfide (7.43 ml) added thereto at -20° C., was stirred for 10 minutes and then allowed to warm to room temperature. The residue obtained by evaporation of the solvent under reduced pressure was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to give methyl 9-oxononanate (5.65 g, 89.9%). 1H-NMR(CDCl3) δ: 1.22-1.59(10H), 2.28(2H, t, J=7.0 Hz), 2.40(2H, dt, J=1.5, 7.0 Hz), 3.64(3H, s), 9.74(1H, t, J=1.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.8% | With sodium thiosulfate; 3-chloro-benzenecarboperoxoic acid In 1,4-dioxane; dichloromethane | (Method B) (Method B) To a solution of 70% methyl oleate (10.0 g) in dichloromethane (50 ml) was added 70% m-chloroperbenzoic acid (16.63 g) while being cooled with ice and then stirred for 1 hour at room temperature. To the reaction mixture was added saturated sodium thiosulfate aqueous solution and then extracted with diethyl ether. The organic layer was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, and then dried over sodium sulfate anhydride. The solvent was evaporated under reduced pressure to give a crude product (12.73 g). Then, to an aqueous solution (5 ml) containing periodic acid dihydrate (13.3 g) was added a solution of the resulting crude product (12.73 g) in dioxane (25 ml) and then stirred for 1 hour at room temperature. The reaction mixture was poured into water and then extracted with diethyl ether. The organic layer was washed with saturated brine, dried over sodium sulfate anhydride, and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to give methyl 9-oxononanate (3.641 g, 82.8%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | To a solution of <strong>[3020-28-8](iodomethyl)triphenylphosphonium iodide</strong> (39.89 g, 75.3 mmol) in anhydrous THF (300 mL) NaHMDS (75.3 mL, 1.0M in THF, 75.3 mmol) was dropwise added and stirred for 10 min at 23 0C. The reaction mixture was cooled to -60 0C and l ,3-dimethyl-3, 4,5, 6-tetrahydro-2( IH)- pyrimidinone (15.3 mL, 126.4 mmol) was dropwise added and immediately cooled to -78 0C. A solution of methyl 8-formyloctanoate 12 (5.6 g, 30.1 mmol) in THF (290 mL) was slowly added to the ylide solution, over 30 min, stirred for 5 min at -78 0C and warmed to 23 C. After 2 hours, the mixture was diluted with hexane (300 mL) and washed with a saturated aqueous solution of NaCl (300 mL). The aqueous layer was extracted with hexane (3x300 mL) and the combined organic layers were dried over Na2SO4, filtered, and evaporated. Flash chromatography on silica gel (CH2Cb:Hexane, 1 : 1) provided (Z)-methyl lO-iododec-9-enoate 13 (7.21 g, 77%) as a colourless oil. 1H NMR (300 MHz, CDCl3) delta 6.16-6. 12 (m, 2H), 3.66 (s, 3H), 2.30 (t, J= 7.3 Hz, 2H), 2.13 (m, 2H), 1.60 (m, 2H), 1.40- 1.20 (m, 8H).13C NMR (75 MHz, CDCl3) delta 174.3, 141.3, 82.2, 51.4, 34.6, 34.0, 29.7, 29.0, 28.8, 27.8, 24.9. MS (APCI): 184 (M- 128)+. Rf= 0.25 (CH2Cl2:Hexane, 1 : 1). | |
67% | 10-Iododec-9(Z)-enioc acid methyl ester (5):NaHMDS (285 mL, 0.57 mol, 2M in THF) was added drop wise to a suspension of CH2IP+PPh3I" (299 g, 0.56 mol) in anhydrous THF (1.5 L) at room temperature. After stirring for five minutes the solution was cooled to -78C and HMPA (139 mL, 0.77 mol) was added drop wise. 9-oxononanoic acid methyl ester 4 (75.0 g, 0.40 mol) was dissolved in anhydrous THF (375 mL) and added drop wise at -78C. The resulting solution was allowed to warm to room temperature and stirred for sixteen hours. Ethyl acetate (1000 mL) and water (500 mL) were added and the layers separated. The aqueous phase was extracted with ethyl acetate (2 x 500 mL). The combined organic layers were washed with water (2 x 500 mL) and brine (500 mL) before being dried (MgSO4), filtered and concentrated in vacuo. The resulting brown oil was dry loaded onto silica (~1 volume) and purified by column chromatography (SiO2, 10% diethyl ether in heptanes) to afford the title compound (64.8 g, 52%) as a yellow oil. The mixed fractions were combined and concentrated before being purified by column chromatography (SiO2, 10% DCM in heptanes) to afford compound 5 (18.4g, 67% combined yield): 1H NMR (400 MHz, Benzene-d6) delta 0.97-1.15 (m, 10H), 1.46-1.49 (m, 2H), 1.93-2.10 (m, 2H), 3.39 (s, 3H), 5.74 (q, IH, J= 7.0, 13.9 Hz), 5.92 (dt, IH, J= 7.3, 1.1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In glycerol; at 180℃; for 15h; | General procedure: An aliquot of 2 +/- 0.01 g of MO or ML were weighed directly into standard glass tubes (200 mm x 12 mm i.d.). The tubes were introduced into a Rancimat vessel containing 8 g of glycerol to facilitate heat transfer, and in turn inserted in the heating block of a Rancimat device previously heated at 180 +/- 1 C. The reaction vessels were left open during heating and bubbling of air was not applied. After 15 h-heating, samples were taken out, shaken, and kept at -20 C until analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
608 mg | Stage #1: formylmethyltriphenylphosphonium chloride With triethylamine In toluene for 1h; Stage #2: methyl ester of azelaic acid aldehyde In toluene at 80℃; for 2h; | 2 A solution of 2.44g of (formylmethyl)triphenylphosphonium chloride in 12ml of toluene was treated with triethylamine (1.1 equiv; 1.11 ml) and stirred for one hour, then a solution of the aldehyde (890mg; 4.78mmol) in toluene was added and the reaction was stirred at 80°C for 2 hours. The mixture was then filtered through Celite and purified on silica gel (15% ethyl acetate/hexane) to yield 608mg of the en-al product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ethylene dibromide (6 drops, 1.74 mmol) were added to Mg turnings (500 mg, 20.6 mmol, -2 eq) in THF (5 ml) under argon. And the mixture was heated to reflux for 20 min. After cooling to room temperature, 4-methylbromopentane (1.38 ml, 10 mmol) in THF (10 ml) was added quickly to the solution of activated Mg turnings. The mixture was then refluxed for 1 h. After cooling to room temperature, the Grignard reagent (1.36 ml, 0.9 mmol, 1 eq) was added to a solution of 10 (170 mg, 0.9 mmol) in THF (1 ml). The reaction was monitored by TLC using 1:4 acetone:hexanes. The reaction was quenched with saturated NH4Cl (10 ml) and extracted with hexanes. Flash column chromatography on silica using a gradient of 0-100% ethyl acetate in hexanes afforded 11 at 60% purity (81.7 mg, 0.3 mmol, 32%). 1H NMR (400 MHz, chloroform-d): (p.p.m.) 3.66 (s, 3H), 3.58 (m, 1H), 2.30 (t, 7.58 Hz, 2H), 1.65-1.49 (m, 4H), 1.47-1.36 (m, 4H), 1.31 (m, 9H), 1.16 (m, 1H), 0.88 (d, 6.64 Hz, 3H), 0.88 (d, 6.64 Hz, 3H |
Tags: 1931-63-1 synthesis path| 1931-63-1 SDS| 1931-63-1 COA| 1931-63-1 purity| 1931-63-1 application| 1931-63-1 NMR| 1931-63-1 COA| 1931-63-1 structure
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