(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehyde → 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbaldehyde (1.0 g, 6.0 mmol) in THF (10 mL) at 0° C. was slowly added propargyl magnesium bromide (1 M, 8.9 mmol). After the reaction was allowed to warm to room temperature overnight 1.5 equivalents of additional propargyl magnesium bromide were added and the reaction was allowed to stir for 6 additional h. The reaction was again cooled to 0° C. and then 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 (0.47 g).

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