Dimethyl Sulfoxide → HCID 14499627, compound

Participants

Reaction Conditions

Reaction Steps

To a solution at -60° C. of oxalylchloride (75.3 g, 0.59 mol) in dry dichloromethane (2 L) under nitrogen, was added a solution of dry DMSO (89.1 g, 1.14 mol) in dry dichloromethane (2 L). 5-Fluoro-4-phthalimidopentanol, 5a, (R=--CH2F) (135 g, 0.54 mol) in CH2Cl2 (2 L) was then added over 15 min. The mixture was stirred 45 min. at -60° C., a solution of triethylamine (352 g, 3.47 mol) in dry CH2Cl2 (2 L) was added slowly (exothermic). The solution was stirred overnight, cooled to -10° C. and water (2 L) added. The organic phase was separated, washed with 4 N HCl, followed by water (3×2 L). The organic phase was separated, dried over Na2SO4 and evaporated. The residue was dissolved in ether, washed with water (3×0.5 L) and dried over Na2SO4. Evaporation of the ether phase gave an oil which was heated at 70° C./0.1 mm Hg to remove traces of DMSO. The title compound (6, R=--CH2F) was obtained as a red oil: 136 g (100%). NMR (1H, CDCl3, 90 MHz).

Provenance & Evidence