Water → 5-Cyano-6-(4-ethoxy-2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid (174 mg, 0.5 mmol) prepared as described in Example 3 above, in THF (10 mL) at −78° C. was added lithium bis(trimethylsilyl)amide (1.2 mL, 1.2 mmol). The resulting mixture was stirred for 30 min at −78° C. and then warmed to room temperature. 4-Ethoxy-2-nitro-5-phenoxy-benzaldehyde (137 mg, 0.5 mmol) was added and the resulting mixture stirred for 4 h at room temperature. Water was added, and the resulting solution was extracted with methylene chloride (3×), washed with brine, dried over Na2SO4, filtered and concentrated. The resulting crude mixture was purified by chromatography (silica gel, 0-2% methanol in methylene chloride) to yield a yellow foam.

Provenance & Evidence