反应 #2271692

反应方程式

water

1-bromo-3-chloropropane

1-(4-hydroxy-3-dimethylaminophenyl)ethanone

sodium hydride

→

black oily liquid

收率 179.0%

1-[4-(3-Chloropropoxy)-3-dimethylaminophenyl] ethanone

收率 179.0%

溶剂

dimethylformamide

dimethylformamide

dimethylformamide

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   其他did not go over 7° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   其他was removed
5. 5
   workup.ADDITIONAfter the addition
6. 6
   workup.STIRRINGthe reaction was stirred for 18 hours at ambient temperature under nitrogen
7. 7
   温度The reaction was chilled to 7° C. in an ice bath
8. 8
   workup.STIRRINGAfter stirring for 5 minutes
9. 9
   萃取the aqueous mixture was extracted with ethyl acetate (5×200 ml)
10. 10
    萃取The ethyl acetate extract
11. 11
    洗涤was washed with water (2×50 ml)
12. 12
    干燥dried with MgSO4
13. 13
    浓缩concentrated

实验过程

To a suspension of sodium hydride (2.3 g, 48.5 mmol of 50% oil dispersion) with dimethylformamide (75 ml), and cooled to 3° C. in an ice-salt bath and under a stream of nitrogen was added, dropwise, 1-(4-hydroxy-3-dimethylaminophenyl)ethanone (8.7 g, 48.5 mmol) dissolved in dimethylformamide (150 ml so that the temperature did not go over 7° C. After the addition was over, the bath was removed and the reaction was stirred at ambient temperature for 45 minutes. The ice bath was reapplied and a solution of 1-bromo-3-chloropropane (8.4 g, 53.4 mmol) in dimethylformamide (25 ml) was added dropwise. After the addition was complete, the reaction was stirred for 18 hours at ambient temperature under nitrogen. The reaction was chilled to 7° C. in an ice bath and water (200 ml) was carefully added. After stirring for 5 minutes, the aqueous mixture was extracted with ethyl acetate (5×200 ml). The ethyl acetate extract was washed with water (2×50 ml), dried with MgSO4, and concentrated to yield 22.2 g of a black oily liquid. The compound was purified by prep HPLC, and combination of appropriate fractions gave 5.0 g of brown oil.

来源