2-Cyclohexen-1-one, 4,4-diphenyl- → (3aRS,7aRS)-7,7-diphenyl-2-(phenylacetyl)-4-perhydroisoindolone

関与物質

反応条件

反応手順

A solution of 4,4-diphenylcyclohex-2-en-1-one (25 g) and 1,3,5-tris-trimethylsilylmethyl-1,3,5-triazine (1.65 g) in 1,1,2-trichloroethane (17 cc) is treated with a solution of phenylacetyl fluoride (1.8 g) in 1,1,2-trichloroethane (5 cc) and the mixture is then heated at 120° C. for 22 hours. The reaction mixture is diluted with dichloromethane (100 cc), washed with saturated sodium bicarbonate solution (100 cc) and with saturated sodium chloride solution (100 cc), dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 3 cm, height 27 cm), eluting with a mixture of cyclohexane and ethyl acetate (90/10 by volume) and collecting 35 cc fractions. Fractions 33 to 36 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-7,7-diphenyl-2-(phenylacetyl)-4-perhydroisoindolone (0.25 g) in the form of white crystals melting at 212° C.

情報源と証拠