تفاعل #1256753

معادلة التفاعل

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

المردود 53.0%

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

المردود 53.0%

المذيبات

1,2-dichloroethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto slowly warm to room temperature over 18 hours
2. 2
   درجة الحرارةThe reaction was cooled to 5° C.
3. 3
   أخرىcautiously quenched with saturated aqueous NaHCO3 (100 mL)
4. 4
   استخلاصThe reaction mixture was extracted with ethyl acetate (100 mL)
5. 5
   استخلاصthe ethyl acetate extract
6. 6
   استخلاصwas extracted with saturated aqueous NaHCO3, water, brine (2×)
7. 7
   تجفيفdried over Na2SO4
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىto give an oil
10. 10
    أخرىThis oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3)

الإجراء التجريبي

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.

المصدر