Tetrahydrofuran → HCID 86753184, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of (1.74 g, 3.13 mmol, 1.2 eq) [[3-(cyclopentyloxy)-4-methoxyphenyl]methyl]triphenylphosphonium bromide in 20 ml dry tetrahydrofuran at -50° C. was added (1.1 ml, 2.78 mmol, 1.1 eq) of 2.5M n-BuLi. The mixture was warmed to 0° C. over 1 hour, cooled to -78° C., and a solution of (600 mg, 2.53 mmol, 1.0 eq)-4-(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)benzaldehyde in 20 ml dry tetrahydrofuran was added dropwise over 10 minutes. The reaction mixture was allowed to warm to room temperature over 18 hours then was quenched with 10 ml saturated NH4Cl solution. The mixture was poured into 200 ml of H2O and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed once with H2O, once with brine, dried over MgSO4, and concentrated to give 2 g of an oil. Flash chromatography eluting with 65% acetone-hexane gave 403 mg of crude product, which was recrystallized from ether-hexane to yield 305 mg, 36%, of the cis product. The trans product was isolated from the chromatography yielding 476 mg, and crystallized from isopropylether to give 415 mg, 39%. Cis-product M.P.: 123°-125° C. Trans-Product M.P.: 156°-158° C. Elemental Analysis of the cis-product: Calc'd for C27H27N3O2 : Calc'd: C, 76.21; H. 6.40; N, 9.87. Found: C, 76.14; H, 6.34; N. 9.71.

Provenance & Evidence