Sodium hydride → HCID 11089976, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (1.3 g, 55 mmol) was suspended in THF (75 mL) and cooled to 0° C. The title compound of Example 1 (14.9 g, 55 mmol) was dissolved in THF (75 mL) and added dropwise to the suspension over 30 minutes. The resulting solution was stirred an additional 30 minutes after which time solid 5-methyl-2-phenyl-4-oxazolyl methyl chloride (10.0 g, 48 mmol) was added in portions over five minutes. The reaction mixture was refluxed for 48 hours, cooled to room temperature and concentrated in vacuo. The residue was dissolved in acetic acid (120 mL) and concentrated HCI (30 mL), and refluxed for five hours. The reaction mixture was cooled to room temperature and poured onto ice-water (300 mL). The aqueous solution was extracted twice with ethyl acetate (500 mL) and the organic extracts were combined and washed with brine (250 mL), dried (MgSO4) and concentrated in vacuo. Purification on silica gel, eluting with hexane/ethyl acetate (4/1), resulted in a crude solid which was further purified by recrystallization from hexane to afford the title compound (11.5 g, 65%) as white crystals. mp 80-81° C. 1HNMR (60 MHz, CDCl3): δ2.2 (s, 3H), 2.8 (m, 2H), 3.2 (m, 2H), 7.2-8.0 (m, 9H).

Provenance & Evidence