تفاعل #1464774

معادلة التفاعل

ammonium chloride

n-butyl lithium

3-benzyloxy-1-bromo-5-fluorobenzene

tetrahydropyran-4-one

→

title compound

المردود 29.4%

4-(3-Benzyloxy-5-fluorophenyl)-4-hydroxytetrahydropyran

المردود 29.4%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred at about -75° C. for about 1 more hour
2. 2
   درجة الحرارةto warm to about 0° C
3. 3
   أخرىthe tetrahydrofuran was evaporated in vacuo
4. 4
   أخرىThe residue was partitioned between water and ethyl acetate
5. 5
   أخرىThe organic phase was separated
6. 6
   تجفيفdried over sodium sulfate
7. 7
   أخرىThe residue was purified by column chromatography on silica gel eluting with methylene chloride/hexanes

الإجراء التجريبي

A solution of 3-benzyloxy-1-bromo-5-fluorobenzene (29.1 g) in 250 ml of tetrahydrofuran was cooled to about -75° C. and n-butyl lithium (1.6M in hexane, 65 ml) was added dropwise.. The mixture was stirred at about -75° C. for about 1 hour and a solution of tetrahydropyran-4-one (10.4 g) was added dropwise. The mixture was stirred at about -75° C. for about 1 more hour then allowed to warm to about 0° C. A saturated aqueous solution of ammonium chloride was added and the tetrahydrofuran was evaporated in vacuo. The residue was partitioned between water and ethyl acetate. The organic phase was separated and dried over sodium sulfate. The residue was purified by column chromatography on silica gel eluting with methylene chloride/hexanes to give 9.2 g of the title compound as an oil.

المصدر