反应详情

Acetylene was bubbled for 50 minutes through a solution of tBuOK (33.8 g; 0.30 mol) in THF (240 ml) at 0° C. The resulting beige suspension was treated with 5-cyclopentylidenepentan-2-one (41.7 g; 0.27 mol) added dropwise for 15 minutes at 0° C. The resulting mixture was warmed gently to room temperature and quenched with saturated NH4Cl (180 ml). The aqueous phase was separated and extracted with MTBE (2×120 ml). The combined organic layers were washed with H2O (240 ml), brine (100 ml), dried over MgSO4, and concentrated in vacuo. Distillation (69° C.-71° C./0.09 torr) afforded 38.95 g (81% yield) of 6-cyclopentylidene-3-methylhex-1-yn-3-ol.

1. additionadded dropwise for 15 minutes at 0° C
2. customquenched with saturated NH4Cl (180 ml)
3. customThe aqueous phase was separated
4. extractionextracted with MTBE (2×120 ml)
5. washThe combined organic layers were washed with H2O (240 ml), brine (100 ml)
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. distillationDistillation (69° C.-71° C./0.09 torr)