(+/-)-1-[1-(Benzyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol → (+/-)-2-(3-{[Tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-5,6,7,8-tetrahydronaphthalen-1-ol
Reaction equation
C([O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][C:10]=1[CH2:19][CH:20]([OH:30])[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])C1C=CC=CC=1>[Pd]>[Si:23]([O:22][CH2:21][CH:20]([OH:30])[CH2:19][C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[C:9]=1[OH:8])([C:26]([CH3:28])([CH3:29])[CH3:27])([CH3:25])[CH3:24]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Treatment of (±)-1-[1-(benzyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol (7.93 g, 0.019 mol) with palladium on carbon (10 wt. %, 0.80 g) generally according to the procedure described for Intermediate 4 gave 5.75 g (92%) of (±)-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-5,6,7,8-tetrahydronaphthalen-1-ol as a colorless oil. Rf=0.55 (silica, ethyl acetate:hexanes 1:3); Anal. calcd. for C19H32O3Si.0.3C4H8O2: C, 66.84; H, 9.55. Found: C, 66.47; H, 9.74.
Sources & evidence
- ORD record
- ord-88305e668d2e42cd99527e1e50481dd9
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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