反応 #166178

反応方程式

LiBH4

(S)-2-(tert-butyl-dimethyl-silanyloxy)-propionic acid ethyl ester

methanol

→

title product

収率 97.0%

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propan-1-ol

収率 97.0%

溶媒

THF

diethyl ether

反応条件

後処理

1. 1
   温度at room temperature for 1.5 hours before cooling to 0° C.
2. 2
   その他carefully quenching with water
3. 3
   ろ過The reaction mixture was filtered
4. 4
   抽出the filtrate extracted with diethyl ether (2×50 mL)
5. 5
   洗浄the combined organic extracts were washed with brine
6. 6
   乾燥dried (MgSO4)
7. 7
   濃縮concentrated in vacuo

実験手順

A 2M solution of LiBH4 (2.77 g, 0.13 mol) in THF (60 mL) was added dropwise to a solution of (S)-2-(tert-butyl-dimethyl-silanyloxy)-propionic acid ethyl ester (22.75 g, 0.10 mol) and methanol (5.15 mL, 0.13 mol) in diethyl ether (500 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and then at room temperature for 1.5 hours before cooling to 0° C. and carefully quenching with water. The reaction mixture was filtered and the filtrate extracted with diethyl ether (2×50 mL), the combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title product as a colourless oil (18.2 g, 97%). 1H NMR (CDCl3, 400 MHz) 3.86-3.77 (1H, m), 3.45-3.37 (1H, m), 3.31-3.22 (1H, m), 1.96-1.85 (1H, m), 1.03 (3H, d, J=6.23 Hz), 0.81 (9H, s), 0.00 (6H, s).

出典