(S)-7-Benzyloxymethoxy-2,6-dimethyl-heptan-2-ol → HCID 20554058, compound

HRID 493064Notes

Reaction equation

HRID 493064 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

HCID 57680493(S)-7-Benzyloxymethoxy-2,6-dimethyl-heptan-2-ol

Product 1

HCID 20554058HCID 20554058, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

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

  1. filtrationThe reaction was then filtered
  2. customthe solvent was evaporated under reduced pressure
  3. 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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