Sodium bis(trimethylsilyl)amide → Methyl 3-iodo-5-{1-[3-iodo-4-methoxy-5-(methoxycarbonyl)phenyl]hept-1-en-1-yl}-2-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

NaN(TMS)2 (1 mL, 1 mmol) was added to an ice cold suspension of hexyltriphenylphosphonium bromide (0.427 g, 1 mmol) in THF (20 mL) and the solution was stirred for 30 min at 0° C. A solution of the benzophenone 39 (0.2 g, 0.33 mmol) in THF (5 mL) was added to the preformed ylide and the solution was stirred at rt overnight. The mixture was partitioned between 1 N HCl (100 mL) and ethyl acetate (100 mL). The organic layer was evaporated and flash chromatographed on SiO2 (230-400 mesh, 50.0 g), eluting with hexanes-ethyl acetate (5:1). The fractions which contained the product were pooled, evaporated, and chromatographed on silica gel (230-400 mesh, 20 g), eluting with hexanes-ethyl acetate (5:1), to give the product 40 (0.022 g, 9%) as an oil: 1H NMR (CDCl3, 300 MHz) δ 7.69 (s, 2H), 7.54 (d, J=2.0 Hz, 1H), 7.52 (d, J=2 Hz, 1H), 6.01 (t, J=7.6 Hz, 1H), 3.93 (s, 3H), 3.89 (s, 3H), 3.88 (s, 3H), 3.85 (s, 3H), 2.05 (q, J=7.3 Hz, 2H), 1.42 (m, 2H), 1.25 (m, 2H), 0.85 (t, J=6.7 Hz, 3H); IR (neat) 2953, 2929, 1742, 1738, 1731, 1713 cm−1; HRFABMS calcd for C25H28I2O6 m/z 677.9975 (M+). Found: m/z 677.9954. Anal. (C25H28I2O60.5EtOAc), C, H.

Provenance & Evidence