Potassium Hydroxide → HCID 67603239, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-cis-3-(4-fluorophenyl)-7-methoxy-4-(4-(2-pyrrolidinoethoxy)phenyl)-chromane (1.0 g, 2.23 mmol) and powdered potassium hydroxide (0.25 g, 4.46 mmol) in dry DMSO (5 ml) was heated to 80° C. for 3 h. The mixture was diluted with water (100 ml) and the products extracted into ethyl acetate (3×100 ml). The combined extracts were washed with water, brine, dried over magnesium sulfate, and evaporated to give the crude multi-component product mixture as an orange gum. The title compound was partially purified by means of column chromatography on silica gel 60, with 5% methanol in dichloromethane as eluent. On evaporation the title compound was isolated as a mixture of the title compound with some of the unreacted cis-isomeric starting material. The title compound was fully purified by means of preparative HPLC: column: YMC 120 Å, 15 μm, 250×10 mm; eluent: 60% methanol in 50 mM aqueous ammonium acetate; flow: 10 ml/min; UV detection at 220 nm. Evaporation of the appropriate fractions gave the title compound as a colourless wax.

Provenance & Evidence