반응 #42191

반응 방정식

(±)-1-[4-(benzyloxy)-2,3-dihydro-1H-inden-5-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol

→

(±)-5-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)indan-4-ol

수율 94.3%

용매

ethanol

반응 조건

후처리

1. 1
   여과The reaction mixture was filtered (celite)
2. 2
   기타the solvent was removed in vacuo
3. 3
   기타to provide a crude oil
4. 4
   기타Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:6)

실험 절차

To a solution of (±)-1-[4-(benzyloxy)-2,3-dihydro-1H-inden-5-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol (9.20 g, 22.29 mmol) in ethanol (200 mL) was added palladium on carbon (1.00 g, 10 wt. %) and the reaction mixture was shaken under an H2 atmosphere (50 psi) for 4 h. The reaction mixture was filtered (celite) and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:6) gave 6.78 g (94%) of (±)-5-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)indan-4-ol as a colorless oil. Rf=0.47 (silica, ethyl acetate:hexanes 1:3); Anal. calcd. for C18H30O3Si: C, 67.03; H, 9.38. Found: C, 66.01; H, 9.33.

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