(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehyde → 1-((1r,2s,5r)-2-Isopropyl-5-methylcyclohexyl)butan-1-ol
Reaction equation
[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]=[O:12])([CH3:3])[CH3:2].[CH2:13]([Mg]Br)[CH2:14][CH3:15]>C1COCC1>[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]([OH:12])[CH2:13][CH2:14][CH3:15])([CH3:3])[CH3:2]Participants
4
Procedure
To a solution of (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbaldehyde (4.64 g, 27.6 mmol) in THF (120 mL) at 0° C. was slowly added propylmagnesium bromide (2 M in THF, 28 mL). After the reaction was allowed to warm to room temperature over 1 h it was again cooled to 0° C. The reaction was quenched with 1 N HCl and partitioned between brine and MTBE. The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica chromatography to give the desired alcohol (1.65 g).