Diethyl Ether → alpha,alpha-Dimethyl-cyclopentanepropanol

Participants

Reaction Conditions

Reaction Steps

262.25 g (1.6 mol) of 3-cyclopentylpropionyl chloride (origin: Aldrich) and 500 ml of anhydrous THF (tetrahydrofuran) were charged into a 5 1 4-neck round bottom flask equipped with a mechanical stirrer and a reflux condenser. Upon cooling to 5° C., 3.2 1 of 1.4 M methyllitium in ether (4.48 mol) was added dropwise to the stirred solution at a rate which maintained the pot temperature between 15-25° C. The reaction mixture was then stirred at room temperature for 26 h and subsequently quenched, at 5° C., with the addition of 350 ml of water. The organic layer was separated and the ether and THF were stripped at reduced pressure. The resulting crude product was fractionally distilled with a 10-plate Oldershaw column at high vacuum to give 162 g of 4-cyclopentyl-2-methyl-2-butanol (purity>97%; yield=65%).

Provenance & Evidence