Reaktion #604563

Reaktionsgleichung

(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

Ausbeute 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

Ausbeute 90.7%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturA 50 ml two-necked round-bottom flask was flame
2. 2
   Sonstigedried
3. 3
   Temperaturto be cooled under nitrogen
4. 4
   SonstigeThe reaction was quenched with 10 ml saturated aqueous sodium bicarbonate
5. 5
   Sonstigeseparated
6. 6
   Extraktionthe aqueous layer was extracted with ethyl acetate
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   FiltrationThe solid was filtered off
9. 9
   Sonstigeorganic solvent was evaporated off under vacuum
10. 10
    SonstigeThe crude product was purified by chromatography
11. 11
    Einengenconcentrated under reduced pressure

Vorschrift

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).

Quelle