(S)-7-Benzyloxymethoxy-2,6-dimethyl-heptan-2-ol → HCID 20554058, compound
Reaction equation
C(OC[O:10][CH2:11][C@@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH3:20][CH:12]([CH2:13][CH2:14][CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[CH2:11][OH:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of an alcohol 7 (1.8 g, 0.01 mol) in ethyl acetate (20 mL) was added Pd/C (10%, 100 mg) at room temperature. The reaction mixture was stirred for 5 days and Pd/C (150 mg) was added 3 times per day. The reaction was then filtered, and the solvent was evaporated under reduced pressure. The crude oil was chromatographed on silica gel using hexane/EtOAc (1:1) as an eluent to give an oily diol 8 (0.95 g, 92%).
Workup
- filtrationThe reaction was then filtered
- customthe solvent was evaporated under reduced pressure
- customThe crude oil was chromatographed on silica gel
Sources & evidence
- ORD record
- ord-2fe352c4f38f43b2a9cd322f78886621
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07534777B2
Reaction notes
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