反応 #336731

反応方程式

hydrochloric acid

tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate

triethylborane

sodium borohydride

→

tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-hydroxybutanoate

収率 55.4%

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas was added at -78° C. over 45 minutes
2. 2
   workup.STIRRINGstirred at -78° C. for 4 hours
3. 3
   抽出the mixture was extracted with ethyl acetate
4. 4
   洗浄washed with saturated saline
5. 5
   乾燥dried over sodium sulfate
6. 6
   濃縮concentrated under reduced pressure

実験手順

To a solution of tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate (10.88 g, 40.0 mmol) in THF (20 ml), a mixture of THF (96.0 ml) and triethylborane 1M in THF) (56.0 ml) was was added at -78° C. over 45 minutes, followed by stirring at -78° C. for 50 minutes. Thereafter, to the resulting mixture, sodium borohydride (1.51 g, 40.0 mmol) was added in one portion and stirred at -78° C. for 4 hours. After adding 1N hydrochloric acid at 0° C., the mixture was extracted with ethyl acetate and washed with saturated saline. The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1) to give pure tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-hydroxybutanoate (6.08 g, 22.16 mmol). Yield, 55%.

出典