反应 #1256753

反应方程式

trifluoroacetic acid

BF3.Et2O

methanesulfonic acid

triethylsilane

Compound 29

4-(3-Ethoxycarbonyl-propyl)-5-oxo-1-(4-methylphenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester

→

compound 30

收率 53.0%

4-(3-Ethoxycarbonyl-propyl)-1-(4-methylphenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester

收率 53.0%

溶剂

1,2-dichloroethane

反应条件

后处理

1. 1
   温度to slowly warm to room temperature over 18 hours
2. 2
   温度The reaction was cooled to 5° C.
3. 3
   其他cautiously quenched with saturated aqueous NaHCO3 (100 mL)
4. 4
   萃取The reaction mixture was extracted with ethyl acetate (100 mL)
5. 5
   萃取the ethyl acetate extract
6. 6
   萃取was extracted with saturated aqueous NaHCO3, water, brine (2×)
7. 7
   干燥dried over Na2SO4
8. 8
   浓缩concentrated in vacuo
9. 9
   其他to give an oil
10. 10
    其他This oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3)

实验过程

Compound 29 (4.76 g, 9.48 mmol) was dissolved in 45 mL of dry 1,2-dichloroethane, cooled to 5° C., and treated with trifluoroacetic acid (1.3 mL), BF3.Et2O (1.4 mL), anhydrous methanesulfonic acid (3.2 mL) and triethylsilane (5.7 mL). The reaction was allowed to slowly warm to room temperature over 18 hours. The reaction was cooled to 5° C. and cautiously quenched with saturated aqueous NaHCO3 (100 mL). The reaction mixture was extracted with ethyl acetate (100 mL) and the ethyl acetate extract was extracted with saturated aqueous NaHCO3, water, brine (2×), dried over Na2SO4, and concentrated in vacuo to give an oil. This oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3) to give 2.43 g (53%) of compound 30 as a colorless oil.

来源