Ethanol → HCID 54480844, compound
Reaction equation
C(C1C=CC(C[CH2:13][CH:14]([O:22]C(=O)C2C=CC=CC=2)[CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=CC=1N)(C)(C)C.C(OC1CCCCC1CCCO[Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])C1C=CC=CC=1.[H][H].C([OH:60])C>[Pd]>[Si:49]([O:22][C@@H:14]([CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[CH2:13][OH:60])([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3.46 g (9.55 mmol) of (S)-[3-benzyloxy-2-(t-butyldimethylsilyloxypropyl)cyclohexane [prepared as described in step (ii) above] in 50 ml of ethanol was vigorously stirred for 5 hours and 20 minutes in a stream of hydrogen and in the presence of 580 mg of 10% w/w palladium-on-charcoal. At the end of this time, the reaction mixture was filtered, and the catalyst was washed with ethanol. The filtrate and the washings were combined and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 180 g of silica gel, using a 1:4 by volume mixture of ethyl acetate and hexane as the eluent, to give 2.54 g (yield 98%) of the title alcohol derivative as a colorless oil.
Workup
- filtrationAt the end of this time, the reaction mixture was filtered
- washthe catalyst was washed with ethanol
- customthe solvent was removed by distillation under reduced pressure
- customThe resulting residue was purified by column chromatography through 180 g of silica gel
- additionby volume mixture of ethyl acetate and hexane as the eluent
Sources & evidence
- ORD record
- ord-2e9f5ea1523d4407a9e7dcab9bad67ab
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05614550
Reaction notes
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