Lithium Hydroxide → HCID 86585391, compound

Participants

Reaction Steps

A mixture of 1.0 g (2.2 mmol) of 4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-6,7-cis-diacetoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoic acid methyl ester. in 20 ml of methyl alcohol and 10 ml of 1 N LiOH was heated at reflux. After 1 h, cooled to room temperature, concentrated under reduced pressure, acidified with 2 N HCl, extracted with ethyl acetate, washed with brine, dried over sodium sulfate and adsorbed onto silica gel. The product was purified by flash chromatography (gradient elution: 20-60% ethyl acetate/hexane with 0.2% acetic acid) to give 560 mg of 4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-6,7-cis-dihydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid.(mp 238.3-241.5) 148.

Provenance & Evidence