反应 #6968

反应方程式

3-butenal diethyl acetal

9-BBN

Na2CO3

3-bromo-4-fluoro-N-cyclopropylbenzamide

→

N-cyclopropyl-3-(4,4-diethoxybutyl)-4-fluorobenzamide

收率 93.4%

溶剂

ethyl acetate

EtOH

benzene

反应条件

后处理

1. 1
   浓缩The mixture was concentrated and to the residue
2. 2
   温度The mixture was then cooled to RT
3. 3
   洗涤washed with water
4. 4
   其他The organic layer was separated
5. 5
   浓缩concentrated
6. 6
   其他The residue was purified by column chromatography (SiO2; EtOAc/hexane 1:3)

实验过程

A solution of 3-butenal diethyl acetal (144 mg, 1 mmol) and 9-BBN (0.5 M in THF, 2.2 mL, 1.1 mmol) was stirred at RT for 1 h. The mixture was concentrated and to the residue were added benzene (2 mL), EtOH (1 mL), aqueous Na2CO3 solution (2M, 1 mL), 3-bromo-4-fluoro-N-cyclopropylbenzamide (127 mg, 0.5 mmol) and Pd(Ph3P)4 (40 mg). The resulting mixture was stirred at 80° C. for 2 h. The mixture was then cooled to RT and diluted with ethyl acetate (10 mL) and washed with water. The organic layer was separated and concentrated. The residue was purified by column chromatography (SiO2; EtOAc/hexane 1:3) to afford N-cyclopropyl-3-(4,4-diethoxybutyl)-4-fluorobenzamide (151 mg, 93%). This material was dissolved in acetone (1 mL) and 3 N HCl solution (0.2 mL) and stirred at RT for 1 h. The mixture was neutralized with NaHCO3 solution and extracted with ethyl acetate (3×5 mL). The organic layer was dried and concentrated to afford N-cyclopropyl-4-fluoro-3-(4-oxo-butyl)-benzamide (110 mg, 94%).

来源