تفاعل #1117517

معادلة التفاعل

3-benzyloxy-5-fluorobromobenzene

magnesium

2-methoxycyclopentanone

3-benzyloxy-5-fluorophenylmagnesium bromide

→

1-(3-benzyloxy-5-fluorophenyl)-2-methoxycyclopentanol

المردود 62.0%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter repetition of the above reaction
2. 2
   أخرىprepared
3. 3
   درجة الحرارةby heating
4. 4
   أخرىThe mixture was evaporated
5. 5
   أخرىthe residue was partitioned between diethyl ether and water
6. 6
   غسيلThe organic layer was washed with water
7. 7
   تجفيفdried (MgSO4)
8. 8
   أخرىevaporated
9. 9
   أخرىThe residue was purified by column chromatography
10. 10
    workup.ADDITIONa 9:1 v/v mixture of methylene chloride and diethyl ether as eluent

الإجراء التجريبي

After repetition of the above reaction, a solution of 2-methoxycyclopentanone (12.5 g) in tetrahydrofuran (10 ml) was added to a solution of 3-benzyloxy-5-fluorophenylmagnesium bromide [prepared by heating a mixture of 3-benzyloxy-5-fluorobromobenzene (31 g), magnesium powder (2.65 g) and tetrahydrofuran (20 ml) to 40° C. for 2 hours] and the mixture was stirred at ambient temperature for 2 hours. The mixture was evaporated and the residue was partitioned between diethyl ether and water. The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 9:1 v/v mixture of methylene chloride and diethyl ether as eluent. There was thus obtained, as a mixture of diastereoisomers, 1-(3-benzyloxy-5-fluorophenyl)-2-methoxycyclopentanol (21.7 g, 62%), as an oil.

المصدر