反応 #83707

反応方程式

(3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl ]-4-perhydroisoindolone

methyllithium

ammonium chloride

ethyl acetate

→

(3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-7-methyl-4,7-perhydroisoindolediol

溶媒

ethyl ether

反応条件

後処理

1. 1
   その他After returning to room temperature
2. 2
   温度the reaction mixture is cooled to +5° C.
3. 3
   乾燥The organic phase is dried over magnesium sulphate
4. 4
   濃縮concentrated to dryness under reduced pressure (2.7 kPa)
5. 5
   その他The residue is chromatographed on a column of silica gel (particle size 0.06-0.20 mm) in ethyl acetate
6. 6
   workup.ADDITIONin a mixture of ethyl acetate and methanol (90/10 by volume)
7. 7
   乾燥After drying under reduced pressure and recrystallization in acetonitrile

実験手順

To a suspension, cooled to -70° C. and under an argon atmosphere, of 0.5 g of (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl ]-4-perhydroisoindolone are slowly added 4 cm3 of 1.6 M methyllithium solution in ethyl ether. After returning to room temperature and stirring for 3 hours, the reaction mixture is cooled to +5° C., followed by addition of 25 cm3 of saturated aqueous ammonium chloride solution and 20 cm3 of ethyl acetate. The organic phase is dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.06-0.20 mm) in ethyl acetate and then in a mixture of ethyl acetate and methanol (90/10 by volume). After drying under reduced pressure and recrystallization in acetonitrile, 0.1 g of (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-7-methyl-4,7-perhydroisoindolediol is obtained, in the form of white crystals melting at 180° C.

出典