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CAS No. : | 300374-83-8 |
Formula : | C10H9F3O3 |
M.W : | 234.17 |
SMILES Code : | FC(F)(F)C(C1=CC=C(OC)C(OC)=C1)=O |
MDL No. : | MFCD01319991 |
InChI Key : | YFISYXOGMSGFRE-UHFFFAOYSA-N |
Pubchem ID : | 2758493 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
With dmap; trifluoroacetic anhydride;AlCl3; In hexane; dichloromethane; ethyl acetate; | 18.1: 2,2,2-Trifluoro-1-(3,4-dimethoxyphenyl)-ethanone 13.8 g (0.10 mol) of 1,2-dimethoxybenzene and 12.2 g (0.10 mol) of 4-dimethylaminopyridine are mixed in 75 ml of CH2Cl2 and cooled in an ice bath. To the solution are added dropwise 21.0 g (0.10 mol) of trifluoroacetic anhydride, followed by 32.0 g (0.24 mol) of AlCl3 by portions. The reaction mixture is stirred at room temperature overnight, poured into ice water, and extracted with CH2Cl2. The organic phase is washed with water, dried over MgSO4, and concentrated. The residue is purified by flash chromatography on silica gel with ethyl acetate and hexane (1:9), yielding 2.9 g of product as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate; In ethanol; water; | 18.2: 2,2,2-Trifluoro-1-(3,4-dimethoxyphenyl)-ethanone oxime 2.9 g (9.7 mmol) of 2,2,2-trifluoro-1-(3,4-dimethoxyphenyl)-ethanone are dissolved in 12 ml of ethanol at 80 C. To the solution are added dropwise 0.83 g (12.0 mmol) of hydroxylammonium chloride and 1.2 g (15.0 mmol) of sodium acetate dissolved in 6 ml of water. The reaction mixture is refluxed for 7.5 hours, poured into ice water, and extracted with ether. The organic phase is washed with water and brine, dried over MgSO4, and concentrated, yielding 2.3 g of 2,2,2-trifluoro-1-(3,4-dimethoxyphenyl)-ethanone oxime. The crude product is used in the next reaction step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | A solution of 5 undecan-2-one (306 mg, 1.8 mmol) in 6 THF (8 mL) was cooled to -78 C. , then 7 LDA (2M solution in THF, 1.05 mL, 2.1 mmol) was added slowly. The mixture was stirred at -78 C. for 45 mins. A solution of 8 <strong>[300374-83-8]2,2,2-trifluoro-1-(3,4-dimethoxyphenyl)ethanone</strong> (234 mg, 1.0 mmol) in THF (2 mL) was added slowly. After stirred at -78 C. for 4 hrs, the mixture was warmed to RT for 30 mins. 20 mL of Sat'd aq. NH4Cl was added. This mixture was extracted with diethyl ether (30 ml) twice. The combined ether layer was washed with brine (20 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by ISCO flash column (0-10% 9 ethyl acetate/hexanes to afford 10 title compound 404 mg (100%). LC/MS: Rf=6.88 min, purity>95%, (M+H)+=404.68. 1H NMR (300 MHz, CDCl3) δ 7.13-7.22 (m, 1H), 6.91-7.05 (m, 1H), 6.83 (d, J=8.50 Hz, 1H), 3.85 (s, 3H), 3.86 (s, 3H), 3.05-3.36 (m, 2H), 2.28-2.58 (m, 2H), 1.40-1.61 (m, 2H), 1.22 (br. s., 12H), 0.86 (t. J=6.45 Hz, 3H) | |
35 mg | To a solution of undecan-2-one (306 mg, 1.8 mmol) in THF(8 mL) at 78 C, LDA (2 M solution in THF, 1.1 mL, 2.2 mmol) wasadded slowly. The mixture was stirred at 78 C for 45 min. Next, asolution of <strong>[300374-83-8]2,2,2-trifluoro-1-(3,4-dimethoxyphenyl)ethanone</strong>(234 mg, 1.0 mmol) in THF (0.5 mL) was added slowly. The solutionwas stirred at 78 C for 3 h 40 mL of saturated NH4Cl was addedand the mixture was extracted from 20 mL of diethyl ether twice.The ether layers were combined and washed with 20 mL of brine,dried over Na2SO4 and concentrated by rotary evaporation. Theresidue was purified by silica chromatography with 0e10% ethylacetate/hexanes. The residue was re-suspended in toluene (4 mL),mixed with pTsOH (48 mg, 0.25 mmol), and heated at 125 C for 1 h.After completion, the mixture was concentrated by rotary evaporationand purified by silica with 0e10% ethyl acetate/hexanes togive the title compound. Yield 35 mg, 0.095 mmol (9.5%). LC/MS:Rf 8.42 min. Purity >95%. 1H NMR (300 MHz, CHLOROFORM-d):d 7.32 (s, J 3.51 Hz, 1H), 7.26 (s, J 3.04 Hz, 1H), 6.98 (s, J 3.30 Hz,1H), 6.66e6.72 (m, 1H), 6.50 (s, 1H), 3.94 (d, J 2.93 Hz, 6H), 2.77(d, J 7.62 Hz, 2H), 1.65 (d, J 7.62 Hz, 3H), 1.23e1.47 (m, 11H),0.83e0.93 (m, 3H), 0.00 (s, 1H). m/z 391.1855 [M Na]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of 2-heptanone-1,1,1,3,3-d5 (238 mg, 2.0 mmol) inTHF (5 mL) at 78 C, LDA (2 M solution in THF, 1.05 mL, 2.1 mmol)was added slowly. The mixture was stirred at 78 C for 45 min.Next, a solution of <strong>[300374-83-8]2,2,2-trifluoro-1-(3,4-dimethoxyphenyl)ethanone</strong>(234 mg, 1.0 mmol) in THF (0.5 mL) was added slowly. Thesolutionwas stirred at 78 C for 3 h 40 mL of saturated NH4Cl wasadded and the mixture was extracted from 20 mL of diethyl ethertwice. The ether layers were combined and washed with 20 mL ofbrine, dried over Na2SO4 and concentrated by rotary evaporation.The residue was purified by silica chromatography with 0e10%ethyl acetate/hexanes. The residue was re-suspended in toluene(4 mL), mixed with pTsOH (61 mg, 0.35 mmol), and heated at 125 Cfor 2 h. After completion, the mixture was concentrated by rotaryevaporation and purified by silica with 0e20% ethyl acetate/hexanesto give the title compound. Yield 99 mg, 0.315 mmol (31.5%).LC/MS: Rf 6.72 min. Purity >95%. 1H NMR (300 MHz, CHLOROFORM-d) d 7.12e7.24 (m, 1H), 7.19 (s, 1H), 7.05 (d, J 1.17 Hz, 1H),6.97 (s, 1H), 6.70e6.88 (m, 1H), 3.95 (d, J 3.51 Hz, 6H), 3.91 (d,J 1.76 Hz, 1H), 2.60 (d, J 6.44 Hz, 1H), 2.51e2.65 (m, 1H), 1.57 (d,J 7.62 Hz, 1H), 1.43 (d, J 7.03 Hz, 1H), 1.18e1.74 (m, 3H), 0.96 (t,J 7.32 Hz, 3H), 1.01 (br. s., 1H). ESI-MS(): m/z 315.59 [M H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of nonan-2-one (255 mg, 1.8 mmol) in THF (8 mL)at 78 C, LDA (2 M solution in THF, 1.1 mL, 2.2 mmol) was addedslowly. The mixture was stirred at 78 C for 45 min. Next, a solutionof 2,2,2-trifluoro-1-(3-methoxyphenyl)ethan-1-one(204 mg, 1.0 mmol) in THF (0.5 mL) was added slowly. The solutionwas stirred at 78 C for 3 h 40 mL of saturated NH4Cl wasadded and the mixture was extracted from 20 mL of diethyl ethertwice. The ether layers were combined and washed with 20 mL ofbrine, dried over Na2SO4 and concentrated by rotary evaporation.The residue was purified by silica chromatography with 0e20%ethyl acetate/hexanes. The residue was re-suspended in toluene(4 mL), mixed with pTsOH (43 mg, 0.25 mmol), and heated at 100 Cfor 5 h. After completion, the mixture was concentrated by rotaryevaporation and purified by silica with 0e20% ethyl acetate/hexanesto give the title compound. Yield 41 mg, 0.132 mmol (13.2%).LC/MS: Rf 7.78 min. Purity >95%. 1H NMR (300 MHz, CHLOROFORM-d) d 7.52 (d, J 8.79 Hz, 1H), 7.18 (s, J 3.54 Hz, 1H), 7.00 (br.s., 1H), 6.84 (d, J 8.20 Hz, 2H), 3.84e3.88 (m, 3H), 2.58 (d,J 7.62 Hz, 2H), 1.50e1.63 (m, 2H), 1.26e1.44 (m, 6H), 0.84e0.97(m, 3H). ESI-MS(): m/z 311.1617 [M H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of 9-hydroxynonan-2-one (791 mg, 5 mmol)benzyl bromide (1.11 g, 6.5 mmol) was added in 50% aqueous sodiumhydroxide (4 mL) and benzene (4 mL) in the presence oftetrabutylammonium hydrogen sulfate (353 mg, 1 mmol) andallowed to stir at room temperature for 5 h. The mixture wasneutralized with 5 N HCl, extracted with ethyl acetate, dried, andconcentrated. The residue was purified by silica chromatographywith 0e20% ethyl acetate/hexanes to yield 9-(benzyloxy)nonan-2-one. The 9-(benzyloxy)nonan-2-one was resuspended in THF(8 mL) at 78 C, and LDA (2 M solution in THF, 1.1 mL, 2.2 mmol)was added slowly. The mixture was stirred at 78 C for 45 min.Next, a solution of <strong>[300374-83-8]2,2,2-trifluoro-1-(3,4-dimethoxyphenyl)ethanone</strong>(234 mg, 1.0 mmol) in THF (0.5 mL) was added slowly. Thesolutionwas stirred at 78 C for 3 h 40 mL of saturated NH4Cl wasadded and the mixture was extracted from 20 mL of diethyl ethertwice. The ether layers were combined and washed with 20 mL ofbrine, dried over Na2SO4 and concentrated by rotary evaporation.The residue was purified by silica chromatography with 0e10%ethyl acetate/hexanes. The residue was re-suspended in toluene(3 mL), mixed with pTsOH (28 mg, 0.16 mmol), and heated at 90 Cfor 5 h. After completion, the mixture was concentrated by rotaryevaporation and purified by silica then, further purified by C18 togive the title compound. Yield 10 mg, 0.022 mmol (2.2%). LC/MS:Rf 7.60 min. Purity >95%. 1H NMR (300 MHz, CHLOROFORM-d)d 7.25e7.37 (m, 7H), 6.97 (s, J 2.55 Hz, 1H), 6.68 (t, J 3.08 Hz, 1H),6.48 (t, J 7.50 Hz, 1H), 4.49 (s, 2H), 3.87e3.99 (m, 7H), 3.47 (t,J 6.44 Hz, 2H), 2.76 (q, J 7.23 Hz, 2H), 2.15 (d, J 12.89 Hz, 1H),1.55e1.70 (m, 5H),1.46 (td, J 3.51, 7.03 Hz, 4H),1.25 (s, 1H), 0.00 (s,1H). ESI-MS(): m/z 447.73 [M H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With potassium hexamethylsilazane; In Triethylene glycol dimethyl ether; at -40℃; for 4h; | General procedure: A test tube containing 1 (0.4 mmol) in triglyme (0.7 mL) was charged with HCF3 (9.9 mL, 1.1 equiv) by a syringe(Figures S1) by cooling in liquid nitrogen under vacuum. KHMDS (160 mg, 2.0 equiv) in triglyme (0.3 mL) wasadded at -40 C, and the reaction mixture was stirred at the same temperature for 4 h. Thereafter, 1M HCl aq. (1.0mL) was added, and the aqueous layer was extracted with CH2Cl2 (1.0 mL × 3). The combined organic layer waswashed with brine, dried over Na2SO4, concentrated under reduced pressure, and purified by column chromatographyon silica gel to give products 2. The commercial grade of triglyme was used without further drying. |
Tags: 300374-83-8 synthesis path| 300374-83-8 SDS| 300374-83-8 COA| 300374-83-8 purity| 300374-83-8 application| 300374-83-8 NMR| 300374-83-8 COA| 300374-83-8 structure
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H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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