Tetrahydrofuran → HCID 11657724, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-BuLi in hexanes (88 ml of 2.5 N solution), diluted with diethyl ether (400 ml), was added over 3 hours to a stirred mixture of phenylphosphine (10.0 g, 90.1 mmol) and the cyclic sulfate (4S,7S)-4,7-diethyl-2,2-dioxo-1,3,2-dioxathian (19.6 g, 0.1 mol, 10% excess) in of THF (1 L), under a nitrogen atmosphere. The mixture was maintained at a temperature of −30° C. during the first half of the addition period, with cooling to −75° C. for the second half. The mixture was then left to warm overnight. After removal of the solvent, pentane (250 ml) and water (100 ml) were added to the residue. The organic layer was dried, and the solvent was removed to leave the phosphetane as a pale yellow oil which was pure with the exception of a small amount of unreacted phenylphosphine as impurity. After distillation (bp.=81° C. at 0.05 mm), 9.94 g of (2R,4R)-2,4-diethyl-1-phenylphosphetane (53% yield based on phenylphosphine) was obtained.

Provenance & Evidence