反应 #80532

反应方程式

( 10c )

N-[1-[[[(1,1-Dimethylethyl)diphenylsilyl]oxy]methyl]-2-hydroxybutyl]Heptanamide

pyridinium dichromate

→

residual brown liquid

收率 81.8%

(S)-N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-oxopropyl]-Heptanamide

收率 81.8%

溶剂

water

N,N-dimethylformamide

反应条件

后处理

1. 1
   萃取extracted with ethyl acetate (3×40 mL)
2. 2
   其他The organic layer is separated
3. 3
   洗涤washed with water and brine
4. 4
   其他dried
5. 5
   其他evaporated

实验过程

A mixture of (10c), (2.30 g, 6.94 mmol) and pyridinium dichromate (10.62 g, 28.2 mmol) in 20 mL of N,N-dimethylformamide is stirred under argon for 18 h. The reaction mixture is diluted with 100 mL of water and extracted with ethyl acetate (3×40 mL). The organic layer is separated, washed with water and brine, dried and evaporated to give 1.87 g of a residual brown liquid. The liquid is purified by chromatography using 1:6 ethyl acetate/hexane to give 997 mg of the desired product as an oil. NMR δ0.83 (S, 9H), 1.61 (m, 2H), 2.22 (t, 2H), 2.23 (s, 3H), 3.82 (dd, 1H), 4.09 (dd, 1H), 4.57 (m, 1H), 6.42 (brd, 1H); MS (FAB) m/z 330 (M+H calc'd for C17H36NO3Si 330).

来源