反应详情

A mixture of 0.7 g (1.58 mmol) of methyl-4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-6-oxo -5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid in 40 ml of MeOH and 20 ml of 1 N LiOH was heated to reflux temperature. After 1 h, the reaction was cooled to room temperature and the MeOH removed under reduced pressure. The aqueous solution was 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: 10-30% ethyl acetate/hexane with 0.2% acetic acid) and by recrystallization (ethyl acetate/hexane) to afford 100 mg (15%) of 4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-6-oxo -5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]-benzoic acid (mp=233-233.5) 133.

1. temperaturewas heated
2. temperatureto reflux temperature
3. customthe MeOH removed under reduced pressure
4. extractionextracted with ethyl acetate
5. washwashed with brine
6. dry with materialdried over sodium sulfate
7. customThe product was purified by flash chromatography (gradient elution: 10-30% ethyl acetate/hexane with 0.2% acetic acid) and by recrystallization (ethyl acetate/hexane)