Dimethylformamide → HCID 131723013, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-[3-(5-Methyl-2-phenyl-4-oxazolyl)-3-methoxypropyl]bromobenzene (1.1 g, 2.8 mmol, prepared as described in Example 15) was dissolved in THF (30 mL), cooled to −78° C. and treated with n-butyllithium (2.5 M in THF, 1.2 mL, 3.0 mmol) dropwise via syringe. Following addition, the reaction mixture was stirred at −78° C. for an additional hour and treated with dry DMF (220 mg, 30 mmol). The reaction mixture was stirred at −78° C. for 90 minutes and at ambient temperature for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water (50 mL), 10% aqueous hydrochloric acid (50 mL), water (50 mL), brine (50 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue was purified on silica gel, eluting with hexane/ethyl acetate (3/1), to afford a viscous oil (580 mg, 62%). 1HNMR (300 MHz, CDCl3): δ2.0 (m, 2H), 2.3 (s, 3H), 2.5 (t, 2H), 3.2 (s, 3H), 4.15 (dd, 1H), 7.3 (m, 3H), 7.4 (d, 2H), 7.8 (d, 2H), 7.9 (m, 2H), 9.9 (s, 1H).

Provenance & Evidence