反応 #1256753

反応方程式

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

収率 53.0%

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

収率 53.0%

溶媒

1,2-dichloroethane

反応条件

後処理

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
   その他cautiously quenched with saturated aqueous NaHCO3 (100 mL)
4. 4
   抽出The reaction mixture was extracted with ethyl acetate (100 mL)
5. 5
   抽出the ethyl acetate extract
6. 6
   抽出was extracted with saturated aqueous NaHCO3, water, brine (2×)
7. 7
   乾燥dried over Na2SO4
8. 8
   濃縮concentrated in vacuo
9. 9
   その他to give an oil
10. 10
    その他This oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3)

実験手順

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.

出典