Dimethyl Sulfoxide → HCID 22507251, compound

Participants

Reaction Steps

Oxalyl chloride (115.0 mmol, 10.0 ml) in CH2Cl2 (200 ml) was cooled to −78° C. under an argon atmosphere. DMSO (240.0 mmol, 17.0 ml) was then added slowly, keeping the internal temperature below −50° C. After completing the addition, the solution was held 20 minutes at −78° C. 3-[1,3]Dioxolan-2-yl-1-(2-trifluoromethylphenyl)-propan-1-ol (32.8 g of crude material prepared above) in CH2Cl2 (30 ml) was added slowly, keeping the internal temperature below −50° C. The mixture was held at −78° C. for 30 minutes, then treated with Et3N (480 mmol, 70.0 ml). The mixture was allowed to warm to room temperature, then washed with water (2×75 ml), then concentrated under reduced pressure to give crude 3-[1,3]dioxolan-2-yl-1-(2-trifluoromethyl-phenyl)-propan-1-one, which may be used without further purification. 1H NMR (CDCl3) δ7.00 (1H, d, J=7.7), 7.63-7.50 (2H, m), 7.44 (1H, d, J=7.4), 4.99 (1H, t, J=4.3), 3.97-3.82 (4H, m), 2.98 (2H, t, J=7.3) 2.12 (2H, dt, J=7.4, 4.3).

Provenance & Evidence