Sodium bis(trimethylsilyl)amide → HCID 18617849, compound

Participants

Reaction Steps

To a cooled slurry (0° C.) of methyltriphenylphosphonium bromide (18.8 g, 52.6 mmol) in THF (60 mL) is added dropwise (1M)sodium bis(trimethylsilyl)amide (52.6 mL, 52.6 mmol) and the resulting mixture stirred for 30 min. To the mixture is added a solution of 2-(4-furan-2-yl-phenyl)-2-methyl-propionaldehyde (5.64 g, 26.3 mmol) (reference example 52) in THF (25 mL) and the resulting mixture stirred for 45 min. The mixture is diluted with ether, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give 6.2 g of title compound as a yellow oil. 1H NMR (CDCl3) δ 1.41 (s, 6H), 5.03 (s, 1H), 5.08 (d, J=7 Hz, 1H), 6.03 (m, 1H), 6.45 (m, 1H), 6.60 (d, J=3 Hz, 1H), 7.36 (d, 8 Hz, 2H), 7.44 (s, 1H), 7.60 (d, J=8 Hz, 2H). MS (EI) m/z 212 (M+).

Provenance & Evidence