Tetrahydrofuran → HCID 19774630, compound

Participants

Reaction Steps

A suspension of methyltriphenylphosphonium bromide (12.24 g, 34.3 mmole) in dry tetrahydrofuran (83 mL) was cooled down to -78° C. (dry ice-acetone) under argon, treated with 1.6M n-butyllithium (18.8 mL, 30.2 mmole, 3.9 eq.) in hexane and stirred at -78° C. for 30 minutes and at 0° (ice water) for 1.0 hour. The reaction mixture was then treated with a solution of Part J compound (1.32 g, 7.76 mmole) in dry tetrahydrofuran (34 mL), stirred at 0° for 30 minutes, allowed to warm up to room temperature and stirred for another 20 hours. The mixture was quenched with 25% NH4Cl (13.9 mL) and the thick aqueous slurry was extracted with ethyl acetate (3×150 mL). The combined organic extracts were dried (anhydrous MgSO4), filtered and evaporated to dryness. The crude product was chromatographed on a silica gel column (Baker, 60-200 mesh, 400 mL), eluting the column with EtOAc:Hexane (1:3) to give title compound as a colorless oil (1.25 g, 95.7%).

Provenance & Evidence