2,4-Dichlorobenzyl chloride → HCID 58109404, compound

Participants

Reaction Steps

To a stirred solution of 6-allyl-6-(4-fluorophenyl)-1,3-oxazinan-2-one (15 mg, 0.064 mmol) and 2,4-dichlorobenzyl chloride (25 mg, 0.13 mmol) in dry DMF (0.5 mL) under N2 was added 60% NaH in oil in small portions until gas evolution ceased. The mixture was stirred overnight at rt and quenched with water (0.5 mL). The mixture was applied to a 10-mL Chem-Elut cartridge and eluted with ether (50 mL). The eluate was evaporated to dryness and the residue was purified by preparative HPLC to afford 6-allyl-3-(2,4-dichlorobenzyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (5.5 mg, 22%). LC-MS Method 1 tR=2.1 min, m/z=394; 1H NMR (CDCl3) 2.30 (2H), 2.60 (m, 2H), 2.96 (m, 1H), 3.08 (m, 1H), 4.44 (d, 1H), 4.65 (d, 1H), 4.75 (1H), 5.06 (m, 2H), 5.67 (m, 1H), 6.86 (d, 1H), 7.08 (3H), 7.30 (3H).

Provenance & Evidence