Dimethyl Sulfoxide → HCID 12487496, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (7.0 mL, 76.6 mmol) in methylene chloride (200 mL) under argon atmosphere at -78° C. was added dropwise dimethylsulfoxide (11.9 mL, 152 mmol). After stirring for 15 minutes 1-hydroxy-1-phenylpent-4-yne (11.14 g, 69.6 mmol) in methylene chloride (20 mL) was added dropwise. After stirring at -78° C. for 1 hour triethylamine (48 mL, 340 mmol) was added and the orange reaction mixture was allowed to warm to room temperature. Water (100 mL) was added, the layers separated, and the organic extract was washed with 1% hydrochloric acid solution (4×100 mL), saturated sodium bicarbonate solution, brine, and dried (MgSO4). Evaporation of solvent under reduced pressure gave a solid which was recrystallized from petroleum ether to afford 5.25 g product. The mother liquors were distilled by Kugelrohr (80° C., 0.1 mm Hg) to give an additional 8.3 g (75 %) of product. 1H NMR (CDCl3) δ: 1.99 (t, J=2.69 Hz, 1H), 2.63 (t, J=7.21 Hz, 1H), 2.64 (t, J=6.17 Hz, 1H), 3.25 (t, J=6.23 Hz, 1H), 3.26 (t, J=7.20 Hz, 1H), 7.44-7.58 (m, 3H), 7.96-7.99 (m, 2H) ppm.

Provenance & Evidence