Tetrahydrofuran → HCID 178497701, compound

Participants

Reaction Steps

A solution of ethyl 3-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]pyrazole-4-carboxylate (from Example 18), (0.4.0 g, 1.1 mmol) was stirred overnight with lithium aluminum hydride (0.18 g, 4.7 mmol). THF (25 mL) was added and stirring was continued for 1 hour. The reaction mixture was then treated successively with water (0.2 mL), 15% aqueous sodium hydroxide (0.2 mL) and water (0.6 mL). The inorganic material was filtered and washed and methylene chloride. The organic solutions were combined and evaporated under reduced pressure. The crude product was purified by flash chromatography over 3.5 g of flash chromatography silica gel. Elution with methylene chloride and 1% methanol/methylene chloride removed some impurities. Elution with 2% methanol/methylene chloride gave 0.21 g (60%) of 3-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]pyrazole carbinol. Pure title compound, mp 88-91°, was obtained by crystallization from ether/hexanes.

Provenance & Evidence