反応 #83689

反応方程式

2-methoxyphenylmagnesium bromide

(3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindolone

ammonium chloride

→

(3aRS,4RS,5RS,7aRS)-2-benzyl-7,7-dimethyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol

収率 35.1%

溶媒

ethyl ether

—

ice

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONis added dropwise, at room temperature
2. 2
   workup.STIRRINGThe reaction mixture is stirred at room temperature for 15 hours
3. 3
   抽出The organic phase is extracted with 3 times 100 cm3 of ethyl ether
4. 4
   乾燥dried over magnesium sulphate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated to dryness under reduced pressure (2.7 kPa)
7. 7
   その他The residue is crystallized in 500 cm3 of petroleum ether

実験手順

To a suspension of 33.8 g of 2-methoxyphenylmagnesium bromide in 75 cm3 of tetrahydrofuran is added dropwise, at room temperature and with stirring, a solution of 6.6 g of (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindolone in 75 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 hours, treated with 200 cm3 of saturated aqueous ammonium chloride solution and taken up in 200 cm3 of ethyl ether and 100 g of ice. The organic phase is extracted with 3 times 100 cm3 of ethyl ether, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 500 cm3 of petroleum ether. 2.8 g of (3aRS,4RS,5RS,7aRS)-2-benzyl-7,7-dimethyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 190° C.

出典