(S)-3,7-dimethyloct-6-en-1-yl methanesulfonate → (R)-2,6-Dimethyl-oct-2-ene
Reaction equation
[CH3:1][C@@H:2]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH2:3][CH2:4]OS(C)(=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:14][C:13](=[CH:12][CH2:11][CH2:10][C@H:2]([CH3:1])[CH2:3][CH3:4])[CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To methanesulfonic acid (S)-3,7-dimethyl-oct-6-enyl ester (60 g, 0.256 mol) in THF (1 L) at 0° C. was added lithium aluminum hydride (3.8 g, 0.128 mol). After 7 hours, a further 3.8 g of lithium aluminum hydride was added and the solution warmed to room temperature. After 18 hours, a further 3.8 g of lithium aluminum hydride was added. After a further 21 hours, the reaction was carefully quenched with 1N citric acid and the solution diluted further with brine. The resultant two phases were separated and the organic phase was dried (MgSO4) and concentrated to afford the titled compound as an oil which was used without further purification. MS, m/z (relative intensity): 139 [M+H, 100%].