Réaction #67892

Équation de réaction

ethyl acetate

((1S,2S,3R,4R)-2-(3-hydroxybenzyl)-4-(tert-butyldimethylsilyoxy)-3-((S)-3-(tert-butyldimethylsilyoxy)octyl)cyclopentyl)methyl 4-methylbenzenesulfonate

sodium hydride

→

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-(tert-butyldimethylsilyoxy)-1-((S)-3-(tert-butyldimethylsilyoxy)octyl)-1H-cyclopenta[b]naphthalen-5-ol

Rendement 87.0%

Solvants

—

ice

THF

Conditions de réaction

Traitement

1. 1
   Températureat reflux
2. 2
   Autreseparated
3. 3
   Extractionthe aqueous layer was extracted with ethyl acetate
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   FiltrationThe solid was filtered off
6. 6
   AutreThe solvent was evaporated off under vacuum
7. 7
   AutreThe crude product was purified by chromatography on silica gel using
8. 8
   workup.ADDITIONa mixture of hexane and ethyl acetate as a gradient eluent

Mode opératoire

A degassed solution of ((1S,2S,3R,4R)-2-(3-hydroxybenzyl)-4-(tert-butyldimethylsilyoxy)-3-((S)-3-(tert-butyldimethylsilyoxy)octyl)cyclopentyl)methyl 4-methylbenzenesulfonate (12.4 g, 0.017 mol) in anhydrous THF (250 ml) at 0° C. under nitrogen was treated with 60% sodium hydride (2.04 g, 0.051 mol). The resulting suspension was stirred for 4 hr at reflux. The reaction was then cooled to 10° C., diluted with ice cold brine (250 ml) and ethyl acetate (500 ml). 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. The solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield: 87%.

Source