反应 #604563

反应方程式

(1S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanol

5-hexenoic acid

N,N′-dicyclohexylcarbodiimide

→

title compound

收率 90.7%

(1S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl hex-5-enoate

收率 90.7%

溶剂

DMF

反应条件

后处理

1. 1
   温度A 50 ml two-necked round-bottom flask was flame
2. 2
   其他dried
3. 3
   温度to be cooled under nitrogen
4. 4
   其他The reaction was quenched with 10 ml saturated aqueous sodium bicarbonate
5. 5
   其他separated
6. 6
   萃取the aqueous layer was extracted with ethyl acetate
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   过滤The solid was filtered off
9. 9
   其他organic solvent was evaporated off under vacuum
10. 10
    其他The crude product was purified by chromatography
11. 11
    浓缩concentrated under reduced pressure

实验过程

A 50 ml two-necked round-bottom flask was flame dried and allowed to be cooled under nitrogen. (1S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanol (1 g, 1.66 mmol) in 10 ml of DMF, 0.05 g (0.33 mmol) of DMAP, 0.21 g (1.83 mmol) of 5-hexenoic acid, and 0.41 g (2.00 mmol) of N,N′-dicyclohexylcarbodiimide were added to the reaction flask. The reaction mixture was heated at 40° C. for 24 hours. The reaction was quenched with 10 ml saturated aqueous sodium bicarbonate. The reaction mixture was phase separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off and organic solvent was evaporated off under vacuum. The crude product was purified by chromatography and then concentrated under reduced pressure to provide 1.05 g of the title compound (90.52% yield).

来源