تفاعل #83689

معادلة التفاعل

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

المردود 35.1%

المذيبات

ethyl ether

—

ice

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

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
   استخلاصThe organic phase is extracted with 3 times 100 cm3 of ethyl ether
4. 4
   تجفيفdried over magnesium sulphate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated to dryness under reduced pressure (2.7 kPa)
7. 7
   أخرىThe residue is crystallized in 500 cm3 of petroleum ether

الإجراء التجريبي

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.

المصدر