(+/-)-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

Participants

Reaction Steps

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.

Provenance & Evidence