5-(S)-methyl-7-(t-butyldimethylsilyloxy)-2-heptene → (3S)-3-Methylheptan-1-OL

HRID 35723Notes

Reaction equation

HRID 35723 reaction equation
[CH3:1][C@H:2]([CH2:7][CH2:8][O:9][Si](C(C)(C)C)(C)C)[CH2:3][CH:4]=[CH:5][CH3:6].[H][H]>[OH-].[OH-].[Pd+2].CO>[CH3:1][C@@H:2]([CH2:3][CH2:4][CH2:5][CH3:6])[CH2:7][CH2:8][OH:9]

Participants

5

Reactant 2

HCID 537803775-(S)-methyl-7-(t-butyldimethylsilyloxy)-2-hepteneHCID 178418361HCID 178418361, compound

Product 1

HCID 12490717(3S)-3-Methylheptan-1-OL

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 74.8 g. of 5-(S)-methyl-7-(t-butyldimethylsilyloxy)-2-heptene in 500 ml. of methanol was added 7.5 g. of 10% palladium hydroxide on carbon and the mixture shaken in a hydrogen atmosphere for 1.5 hours at 50 psi. The catalyst was filtered and the solvent removed under vacuum, 30 g.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent removed under vacuum, 30 g

Sources & evidence

ORD record
ord-01daf8a69ff143439ee15aa2712ff87a
Source dataset
uspto-grants-1988_08
Patent number
US04767743

Reaction notes

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