(+)-6-Methyl-5-hepten-2-ol → (2S)-6-Methylheptan-2-OL
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
Product 1
Reagents, catalysts & solvents 2
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
- customfitted with a magnetic stirrer
- customThe flask was evacuated
- customThe crude reaction mixture
- filtrationwas filtered
- 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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