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171230-81-2

171230-81-2 Structure

171230-81-2 Structure
IdentificationBack Directory
[Name]

(R)-methyl 2-(tert-butyldimethylsilyloxy)propanoate
[CAS]

171230-81-2
[Synonyms]

(R)-methyl 2-(tert-butyldimethylsilyloxy)propanoate
Methyl (R)-2-[(tert-Butyldimethylsilyl)oxy]propanoate
methyl (2R)-2-[tert-butyl(dimethyl)silyl]oxypropanoate
(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propionic acid methyl ester
Propanoic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester, (2R)-
[Molecular Formula]

C10H22O3Si
[MDL Number]

MFCD28402584
[MOL File]

171230-81-2.mol
[Molecular Weight]

218.37
Chemical PropertiesBack Directory
[Boiling point ]

211.4±23.0 °C(Predicted)
[density ]

0.911±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Synthesis]

Methyl (R)-(+)-lactate

17392-83-5

tert-Butyldimethylsilyl chloride

18162-48-6

(R)-methyl 2-(tert-butyldimethylsilyloxy)propanoate

171230-81-2

GENERAL STEPS: A mixture of methyl D-lactate (5.1 g, 48.99 mmol), dichloromethane (50 mL), imidazole (5 g, 75 mmol), and tert-butyldimethylchlorosilane (8.85 g, 58.79 mmol) was stirred for 2 hours at room temperature. After completion of the reaction, the mixture was diluted with water and extracted three times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by medium pressure liquid chromatography (MPLC), using a petroleum ether solution of 5% ethyl acetate as eluent, to afford methyl (R)-2-((tert-butyldimethylsilyl)oxy)propionate (10.67 g, 100% yield) as a colorless oil.

[References]

[1] Patent: WO2015/171610, 2015, A2. Location in patent: Paragraph 000507
[2] Chemical Communications, 1997, # 13, p. 1219 - 1220
[3] Patent: WO2016/154533, 2016, A1. Location in patent: Paragraph 00176
[4] Tetrahedron Asymmetry, 2012, vol. 23, # 2, p. 117 - 123
[5] European Journal of Organic Chemistry, 2013, # 3, p. 525 - 532
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