反应详情

温度

25 °C

A solution of phenylmagnesium bromide (prepared starting from 3.14 g of bromobenzene and 0.48 [lacuna] of magnesium in 30 cm3 of ether) is added to a suspension of 4.09 g of (3aRS,7aRS)-7,7-diphenyl-2-phenylacetylperhydroisoindol-4-one in 50 cm3 of tetrahydrofuran. The reaction mixture is stirred at 25° C. for 1 hour and then heated under reflux for 2.5 hours, cooled and treated with 150 cm3 of a saturated solution of ammonium chloride. The organic phase is washed with water (2×100 cm3). The aqueous phases are extracted with 100 cm3 of ethyl acetate. The combined organic phases are washed with 100 cm3 of a saturated solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 30 cm3 of acetonitrile to give 2.9 g of (3aRS,4RS,7aRS)-2-phenylacetyl- 4,7,7-triphenylperhydroisoindol-4-ol in the form of white crystals which melt at 270° C.

1. temperatureheated
2. temperatureunder reflux for 2.5 hours
3. temperaturecooled
4. washThe organic phase is washed with water (2×100 cm3)
5. extractionThe aqueous phases are extracted with 100 cm3 of ethyl acetate
6. washThe combined organic phases are washed with 100 cm3 of a saturated solution of sodium chloride
7. dry with materialdried over magnesium sulphate
8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
9. customThe residue is crystallized in 30 cm3 of acetonitrile