反応 #1330390

反応方程式

(+)-(1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol

→

(+)-(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol

溶媒

toluene

反応条件

後処理

1. 1
   ろ過The reaction mixture was then filtered
2. 2
   濃縮concentrated to a small volume
3. 3
   その他purified by silica gel column chromatography with a 0–25% ethyl acetate in hexanes gradient

実験手順

A solution of (+)-(1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol (1.43 g, 6.67 mmol) (from Example 29a supra) and Wilkinson's catalyst (1.23 g, 1.33 mmol) (Aldrich) in toluene (55 mL) was subjected to atmospheric pressure hydrogenation for 16.5 hours. The reaction mixture was then filtered, concentrated to a small volume, and purified by silica gel column chromatography with a 0–25% ethyl acetate in hexanes gradient to give (+)-(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol as a colorless oil. (Yield 745 mg, 61%).

出典