Dimethyl Sulfoxide → HCID 12112437, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (4.46 g, 35.13 mmol) and methylene chloride (300 mL) at −78° C. was added dimethyl sulfoxide (3.29 g, 42.15 mmol) over 15 min. After 15 min at −78° C., a solution of N-[5-fluoro-2-hydroxymethylphenyl]benzenepropanamide from Step 2 (3.20 g, 11.7 mmol) and methylene chloride (300 mL) was added over 10 min. After 45 min at −78° C., triethylamine (8.53 g, 84.3 mmol) was added and the reaction was warmed to 23° C. After 20 min at 23° C., the reaction was washed with sat'd NaHCO3 (2×100 mL), brine (1×100 mL) and dried (MgSO4). After concentration in vacuo, the crude residue was purified by flash chromatography (ethyl acetate: hexane 1:3) which afforded the aldehyde as an oil (2.71 g, 85.4%): 1H NMR (CDCl3) δ2.79 (t, J=7 Hz), 3.06-3.16 (m), 6.85-6.93 (m), 7.17-7.37 (m), 7.63-7.69 (m), 8.52-8.58 (m), 9.84 (s).

Provenance & Evidence