(+/-)-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
Reaction equation
C([O:8][C:9]1[C:17]([CH2:18][CH:19]([OH:29])[CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2)C1C=CC=CC=1>C(O)C.[Pd]>[Si:22]([O:21][CH2:20][CH:19]([OH:29])[CH2:18][C:17]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][C:10]=2[C:9]=1[OH:8])([C:25]([CH3:27])([CH3:28])[CH3:26])([CH3:24])[CH3:23]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- filtrationThe reaction mixture was filtered (celite)
- customthe solvent was removed in vacuo
- customto provide a crude oil
- customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:6)
Sources & evidence
- ORD record
- ord-677e6d36d10b4b39ba0eeecac87db0f5
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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