3,4-dihydro-2H-pyran → HCID 13836887, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,3-dihydropyran (2.0 g, 23.8 mmol) in dry THF (50 mL) was added tert-BuLi (26.2 mmol) at -78° C. and the resulting solution was stirred at 0° C. for 1 hour. The mixture was cooled to -78° C. and tributylstannyl chloride (5.53 g, 17.0 mmol) was added and stirring was continued for fifteen minutes at which time the reaction mixture was diluted with water and extracted 3× with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The crude product was filtered through a plug of silica gel to yield 5.23 g (59%) of the title compound as a clear liquid.

Provenance & Evidence