反应 #9334

反应方程式

9-1

(Z)-7-[(1R,2S,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-2-(4-hydroxymethyl-phenyl)-cyclopentyl]-hept-5-enoic acid methyl ester

NMO

→

9-2

收率 79.7%

(Z)-7-[(1R,2S,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-2-(4-formyl-phenyl)-cyclopentyl]-hept-5-enoic acid methyl ester

收率 79.7%

溶剂

dichloromethane

反应条件

后处理

1. 1
   workup.WAITfor 1 h at room temperature
2. 2
   过滤The mixture was then filtered through a pad of silica gel
3. 3
   洗涤washing with ethyl acetate
4. 4
   其他The solvents were evaporated
5. 5
   其他the residue was purified by flash chromatography on silica gel (10% ethyl acetate/hexanes)

实验过程

An ice cold mixture of 9-1 (43 mg, 0.089 mmol), 4 Å molecular sieves (56 mg) and NMO (16 mg, 0.14 mmol) in dichloromethane (0.5 mL) was treated with TPAP (3 mg, 0.009 mmol). The mixture was stirred for 5 min. at 0° C. and then for 1 h at room temperature. The mixture was then filtered through a pad of silica gel, washing with ethyl acetate. The solvents were evaporated and the residue was purified by flash chromatography on silica gel (10% ethyl acetate/hexanes) to give 9-2 (34 mg, 79%).

来源