반응 #604563

반응 방정식

(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

수율 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

수율 90.7%

용매

DMF

반응 조건

후처리

1. 1
   온도A 50 ml two-necked round-bottom flask was flame
2. 2
   기타dried
3. 3
   온도to be cooled under nitrogen
4. 4
   기타The reaction was quenched with 10 ml saturated aqueous sodium bicarbonate
5. 5
   기타separated
6. 6
   추출the aqueous layer was extracted with ethyl acetate
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과The solid was filtered off
9. 9
   기타organic solvent was evaporated off under vacuum
10. 10
    기타The crude product was purified by chromatography
11. 11
    농축concentrated under reduced pressure

실험 절차

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).

출처