反应详情

温度

3 °C

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-dimethylamino-phenyl)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.

1. additionwas added
2. customdid not go over 7° C
3. additionAfter the addition
4. customwas removed
5. additionAfter the addition
6. stirringthe reaction was stirred for 18 hours at ambient temperature under nitrogen
7. temperatureThe reaction was chilled to 7° C. in an ice bath
8. stirringAfter stirring for 5 minutes
9. extractionthe aqueous mixture was extracted with ethyl acetate (5×200 ml)
10. extractionThe ethyl acetate extract
11. washwas washed with water (2×50 ml)
12. dry with materialdried with MgSO4
13. concentrationconcentrated