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

Boiling point:

211.4±23.0 °C(Predicted)

Density 

0.911±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

(R)-methyl 2-(tert-butyldimethylsilyloxy)propanoate Usage And Synthesis

Synthesis

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