Tetrahydrofuran → HCID 11657724, compound

Temperature

-30 °C

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.

1. temperaturewith cooling to −75° C. for the second half
2. waitThe mixture was then left
3. temperatureto warm overnight
4. customAfter removal of the solvent, pentane (250 ml) and water (100 ml)
5. additionwere added to the residue
6. customThe organic layer was dried
7. customthe solvent was removed

ORD record

ord-7438bba36c514606a637ff90b7fd8308

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06545183B1