13937-08-1|Diethyl 2-hydroxymalonate| Ambeed

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Quality Control of [ 13937-08-1 ] Purity: 95% SDS Specification

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Product Details of [ 13937-08-1 ]

CAS No. :	13937-08-1
Formula :	C₇H₁₂O₅
M.W :	176.17
SMILES Code :	O=C(OCC)C(O)C(OCC)=O
MDL No. :	MFCD04038932
InChI Key :	VXZQTXSCMRPKMH-UHFFFAOYSA-N
Pubchem ID :	139648

Safety of [ 13937-08-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 13937-08-1 ]

* 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.

Downstream synthetic route of [ 13937-08-1 ]

[ 13937-08-1 ] Synthesis Path-Downstream 1~35

1
[ 74-89-5 ]
[ 13937-08-1 ]
hydroxy-malonic acid bis-methylamide [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1910,vol. 29,p. 121.

2
[ 51-64-9 ]
[ 13937-08-1 ]
[ 112350-94-4 ]

References: [1]Journal of the American Chemical Society,1958,vol. 80,p. 6060,6063.
Journal of the American Chemical Society,1959,vol. 81,p. 203,207.

3
[ 13937-08-1 ]
2-hydroxymalonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97.5%	With ammonium hydroxide; at 90℃; for 3h;	176g of 2-hydroxymalonic acid diethyl ester (1mol) and 250g, a concentration of 28wt% aqueous ammonia (2mol) mixed, and then heated to 90 , the reaction 3h.After the reaction was completed, water was added and the mixture was extracted three times with ethyl acetate. The organic layer was spin-dried,115 g of 2-hydroxymalonamide were obtained in a yield of 97.5%.

References: [1]Patent: CN106883233,2017,A .Location in patent: Paragraph 0032; 0035; 0036.
[2]Chemische Berichte,1884,vol. 17,p. 782.

4
[ 13937-08-1 ]
[ 609-09-6 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1910,vol. 29,p. 121.

5
[ 545-26-6 ]
[ 13937-08-1 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1910,vol. 29,p. 121.

6
[ 609-09-6 ]
[ 13937-08-1 ]

References: [1]Bulletin de la Societe Chimique de France,1937,vol. <5> 4,p. 31,41.
[2]Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine,1932,vol. 1/,p. 49.
Chemisches Zentralblatt,1933,vol. 104,p. 946.
[3]Chemical Communications,2006,p. 1218 - 1220.
[4]Chemical Communications,2013,vol. 49,p. 1184 - 1186.

7
[ 80-69-3 ]
[ 64-17-5 ]
[ 13937-08-1 ]

References: [1]Journal of the American Chemical Society,1961,vol. 83,p. 4228 - 4233.
[2]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 1412 - 1417.

8
[ 5468-23-5 ]
[ 13937-08-1 ]

References: [1]Israel Journal of Chemistry,1971,vol. 9,p. 89 - 103.
[2]Journal of Organic Chemistry,1990,vol. 55,p. 4515 - 4516.
[3]Journal of Physical Chemistry,1987,vol. 91,p. 426 - 433.

9
[ 685-87-0 ]
[ 13937-08-1 ]

References: [1]Monatshefte fur Chemie,1989,vol. 120,p. 907 - 912.
[2]Journal of Organic Chemistry,1990,vol. 55,p. 4515 - 4516.

10
[ 109-92-2 ]
[ 13937-08-1 ]
[ 128302-74-9 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 4515 - 4516.

11
[ 93-04-9 ]
[ 609-08-5 ]
[ 27581-07-3 ]
[ 118647-58-8 ]
[ 118647-59-9 ]
[ 13937-08-1 ]

References: [1]Gazzetta Chimica Italiana,1988,vol. 118,p. 405 - 408.
[2]Gazzetta Chimica Italiana,1988,vol. 118,p. 405 - 408.

12
[ 105-53-3 ]
[ 13937-08-1 ]

Yield	Reaction Conditions	Operation in experiment
96.6%	With 3,3-dimethyldioxirane; nickel diacetate; In ethanol; for 5h;Reflux;	160g of diethyl malonate (1mol) was dissolved in 300mL of ethanol,Add 111g ofDimethyldioxirane (1.5 mol) and 0.5 g of nickel acetate,Then heated to reflux, the reaction 5h.After the reaction, the ethanol is evaporated to dryness, water is added,Extract with ethyl acetate three times and spin the organic layer to 170 gDiethyl 2-hydroxymalonate was obtained in a yield of 96.6%.
33%	With Oxone; In aq. phosphate buffer; water; ethyl acetate; acetone; at 25℃;pH 8.0;	General procedure: To a round-bottomed flask containing alkene 118(1.0 mmol), ethyl acetate (10 mL), acetone (5.0 mL) andphosphate buffer (1.0 mol L-1 K2HPO4/KH2PO4, pH 8,10 mL), under magnetic stirring, was added a solution ofOxone (1.3 mmol for 1a or 1.5 mmol for 1b) in water(5.0 mL) over a period of 1 h. The reaction mixture wasstirred until TLC (hexane/EtOAc, 80:20, v/v) showedcompletion of the reaction (see below). The insolublesolid was separated by filtration under reduced pressureand washed with EtOAc. The filtrate was washed with1.0 mol L-1 Na2S2O3 and brine, dried over anhydrousNa2SO4, and concentrated under reduced pressure to givethe epoxides as pale yellow oil. The crude mixture waspurified by silica gel chromatography (hexane:EtOAc,80:20, v/v) to provide epoxides 2a and 2b.

References: [1]Patent: CN106883233,2017,A .Location in patent: Paragraph 0032; 0033; 0034.
[2]Journal of the Brazilian Chemical Society,2019,vol. 30,p. 1779 - 1787.
[3]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 609 - 613.

13
[ 6313-33-3 ]
[ 13937-08-1 ]
4,5,6-trihydroxypyrimidine [ No CAS ]

References: [1]Journal of Physical Chemistry,1987,vol. 91,p. 426 - 433.

14
[ 51255-12-0 ]
[ 13937-08-1 ]
3,5-bis-O-benzoyl-2-deoxy-1-O-(2-diethylmalonyl)-β-D-erythro-pentofuranose [ No CAS ]
3,5-bis-O-benzoyl-2-deoxy-1-O-(2-diethylmalonyl)-α-D-erythro-pentofuranose [ No CAS ]

References: [1]Tetrahedron,1998,vol. 54,p. 8223 - 8240.

15
[ 97614-44-3 ]
[ 13937-08-1 ]
3,5-bis-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose [ No CAS ]
3,5-bis-O-benzoyl-2-deoxy-1-O-(2-diethylmalonyl)-2-fluoro-α-D-arabino-pentofuranose [ No CAS ]

References: [1]Tetrahedron,1998,vol. 54,p. 8223 - 8240.

16
[ 508210-05-7 ]
[ 13937-08-1 ]
[ 183550-77-8 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 3982 - 3993.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 1 1,800 ml of absolute ethanol is saturated with HCl gas at room temperature and then, at a maximum of 30 C., first 537 g (trimethylsilyloxy)tricyanomethane are added dropwise and, after stirring for 30 minutes, 54 g of water are added dropwise. After heating at the reflux temperature for 1 hour, followed by cooling, the NH4 Cl is filtered off with suction and the filtrate is concentrated in vacuo. The liquid residue is distilled in vacuo (over a 1 meter long Vigreux column). 316 g (55% of theory) of diethyl tartronate of boiling point 111-113 C./16 mbar are obtained.
		EXAMPLE 2 300 ml of anhydrous ethanol are saturated with HCl gas at 10 C. and then, at 0 C., 102 g of (trimethylsilyloxy)tricyanomethane are added. The mixture is then stirred at 15 C. for 1 hour and subsequently diluted with 300 ml of water. After stirring for 30 minutes, ice-water is added and the mixture is extracted with methylene chloride. Working up the methylene chloride extract and vacuum distillation of the residue provides 86 g (50% of theory) of diethyl tartronate of boiling point 112-113 C./16 mbar.

19
[ 64-17-5 ]
tartronate barium [ No CAS ]
[ 13937-08-1 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1910,vol. 29,p. 121.

20
[ 64-17-5 ]
tartronate calcium [ No CAS ]
[ 13937-08-1 ]

References: [1]Chemische Berichte,1884,vol. 17,p. 782.

21
[ 64-17-5 ]
tartronate sodium [ No CAS ]
[ 13937-08-1 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1910,vol. 29,p. 121.

22
[ 79-17-4 ]
[ 13937-08-1 ]
[ 56-09-7 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 1412 - 1417.

23
[ 6313-33-3 ]
[ 13937-08-1 ]
[ 98020-41-8 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 1412 - 1417.

24
[ 13507-15-8 ]
[ 13937-08-1 ]
[ 98021-25-1 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 1412 - 1417.

25
[ 2136-75-6 ]
[ 21204-67-1 ]
[ 13937-08-1 ]
methyl (triphenylphosphoranylidine) acetate [ No CAS ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 5489 - 5492.

26
[ 2136-75-6 ]
[ 1439-36-7 ]
[ 13937-08-1 ]
[ 66085-96-9 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 5489 - 5492.

27
[ 105-53-3 ]
alkyl sulfate [ No CAS ]
[ 13937-08-1 ]

References: [1]Journal of Physical Chemistry,1987,vol. 91,p. 426 - 433.

28
[ 864464-02-8 ]
[ 13937-08-1 ]
[ 864464-03-9 ]

References: [1]Patent: WO2005/85230,2005,A1 .Location in patent: Page/Page column 52-53.

29
farnesyl bromide [ No CAS ]
[ 13937-08-1 ]
[ 1214275-20-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 543 - 556.

30
[ 50-00-0 ]
[ 13937-08-1 ]
[ 1265520-63-5 ]

Yield	Reaction Conditions	Operation in experiment
		Into an ice-cooled suspension of paraformaldehyde (1.82g; 1.2 eq.) and <strong>[13937-08-1]diethyl 2-hydroxymalonate</strong> (1Og; 1 eq.) , 5.7 ml (1.75 eq.) thionyl chloride and subsequently, 3.6 ml (1.6 eq.) concentrated sulfuric acid were added drop- wise. After 3 hours, the reaction mixture was added to ice and neutralized with NaHCO3. The extraction was performed with diethyl ether, and the resulting solution was dried with Na2SO4. After removal of the solvent, about 8g of the raw product were obtained.
		EXAMPLE 1General procedure for the preparation of the compound of formula (I): EtOOC-CH (OCH2Cl)-COOEtProcedure A: Into an ice-cooled suspension of paraformaldehyde (1.82 g; 1.2 eq.) and <strong>[13937-08-1]diethyl 2-hydroxymalonate</strong> (10 g; 1 eq.), 5.7 ml (1.75 eq.) thionyl chloride and subsequently, 3.6 ml (1.6 eq.) concentrated sulfuric acid were added drop-wise. After 3 hours, the reaction mixture was added to ice and neutralized with NaHCO3. The extraction was performed with diethyl ether, and the resulting solution was dried with Na2SO4. After removal of the solvent, about 8 g of the raw product were obtained.Procedure B: Procedure A was repeated but using instead Solkane 365 mfc for performing the extraction. Comparable results were obtained.Table 1 shows the influence of different parameters; e.g. purity of the <strong>[13937-08-1]diethyl 2-hydroxymalonate</strong> on the selectivity of the reaction, using procedure A.

References: [1]Patent: WO2011/18466,2011,A1 .Location in patent: Page/Page column 12.
[2]Patent: US2012/157708,2012,A1 .Location in patent: Page/Page column 5.

31
(2-bromoethyl)(diphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]
[ 13937-08-1 ]
[ 1384465-73-9 ]

References: [1]Synthesis,2012,vol. 44,p. 1584 - 1590.

32
[ 13937-08-1 ]
[ 1421338-37-5 ]

References: [1]Chemical Communications,2013,vol. 49,p. 1184 - 1186.

33
[ 13937-08-1 ]
[ 1421338-38-6 ]

References: [1]Chemical Communications,2013,vol. 49,p. 1184 - 1186.

34
[ 13937-08-1 ]
[ 1421338-45-5 ]

References: [1]Chemical Communications,2013,vol. 49,p. 1184 - 1186.

35
[ 13937-08-1 ]
[ 1421338-41-1 ]

References: [1]Chemical Communications,2013,vol. 49,p. 1184 - 1186.

Historical Records

Technical Information

• Acyl Group Substitution • Appel Reaction • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chugaev Reaction • Complex Metal Hydride Reductions • Corey-Kim Oxidation • Dess-Martin Oxidation • Ester Cleavage • Heat of Combustion • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Swern Oxidation

Related Functional Groups of
[ 13937-08-1 ]

Aliphatic Chain Hydrocarbons

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Methyl 2,3-dihydroxypropanoate

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Alcohols

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Propane-1,3-diyl bis(2-hydroxypropanoate)

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(S)-Methyl 2,3-dihydroxypropanoate

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H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
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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CAS No.: 13937-08-1

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