Sodium hydride → HCID 17981766, compound

Participants

Reaction Steps

To a solution of 4-phenylimidazole (7.49 g, 51.9 mmol) in DMF (30 mL) cooled to 0° C. under nitrogen add portionwise NaH (95%, 2.56 g, 101 mmol). After 10 minutes, add p-methoxybenzyl chloride (PMBCl) (7.50 mL, 55.3 mmol) dropwise. Stir for 5 hours, quench with MeOH (5 mL), dilute with water (100 mL), and extract with CH2Cl2 (2×100 mL). Dry the combined organic layers (Na2SO4) and concentrate in vacuo to a volume of 80 mL, affording 12.2 g (89% yield) after crystallization. MS(ES+): m/z=265 (M+H)+

Provenance & Evidence