(S)-(+)-6-Methyl-5-hepten-2-ol → (2S)-6-Methylheptan-2-ol

HRID 414892Notes

Reaction equation

HRID 414892 reaction equation
[CH3:1][C:2]([CH3:9])=[CH:3][CH2:4][CH2:5][C@@H:6]([OH:8])[CH3:7]>[Pd].CO>[CH3:1][CH:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C@@H:6]([OH:8])[CH3:7]

Participants

4

Reactant 1

HCID 6971127(S)-(+)-6-Methyl-5-hepten-2-ol

Product 1

HCID 12583653(2S)-6-Methylheptan-2-olYield 866.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5% Palladium on carbon (0.02 g), (2S)-6-methylhept-5-en-2-ol (4.0 g, 3 mmol) and methanol (20 mL) were added to a 50 mL round-bottomed flask fitted with a magnetic stirrer. The flask was evacuated and then pressurised with 1 bar of hydrogen from a balloon. This was repeated three times then the reaction mixture was stirred for 8 hours at room temperature under hydrogen. The crude reaction mixture was filtered and the solvent removed in vacuo to yield (2S)-6-methylheptan-2-ol (3.4 g, 26 mmol, chemical yield 85%), suitable for the next stage.

Workup

  1. customfitted with a magnetic stirrer
  2. customThe flask was evacuated
  3. customThe crude reaction mixture
  4. filtrationwas filtered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1766064b1bdb44bcaf3f250697978349
Source dataset
uspto-grants-2012_01
Patent number
US08088725B2

Reaction notes

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