HCID 11013136, compound → (S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-hexan-1-ol
Reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH3:23])[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[C:19]([Si:16]([CH3:18])([CH3:17])[O:15][CH2:14][C@@H:13]([CH3:23])[CH2:12][CH2:11][CH2:10][CH2:9][OH:8])([CH3:21])([CH3:22])[CH3:20]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 64.0 g (0.19 mol) of the benzylether VIII in 500 ml of THF was hydrogenated (3.5 bar) over 7.0 g of 20% Pd(OH)2/C for 30 min at ambient temperature. The catalyst was removed by filtration and the filtrate was concentrated to afford alcohol IX as colorless oil (46.9 g, 100%). Rf=0.33 (SiO2, 1:1 heptane-TBME).