Propanoic acid, methyl ester synthesis

Yield:361547-56-0 100%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide at 20; for 12 h;

Steps:

4.E.1

A solution of methyl 3-hydroxy-2,2-dimethylpropanoate (5.00 g, 38 mmol), N, N-diisopropylethylamine (7.30 g, 57 mmol) and tert- butyldimethylchlorosilane (6.80 g, 45 mmol) in dry DMF (70 mL) was stirred at room temperature for 12 h. The reaction solution was quenched with water (225 mL) and extracted with diethyl ether (3 x 50 mL). The combined organic extracts were washed with water (100 mL), brine (100 mL), then dried over MgSO₄. Concentration under reduced pressure afforded methyl 3-(tert-butyldimethylsilyloxy)-2,2- dimethylpropanoate as colorless oil (9.36 g, 100%). It was used in the next step without further purification. ¹H NMR (300 MHz, CDCl₃) δ 3.64 (s, 3H), 3.55 (s, 2H), 1.13 (s, 6H), 0.85 (s, 9H), 0.0 (s, 6H).

References:

WO2010/54058,2010,A1 Location in patent:Page/Page column 80