反应详情

0.077 g (1.93 mmol) sodium hydride as a 60% dispersion in mineral oil is suspended in 15 ml absolute DMF, stirred at room temperature for 10 min, mixed with a solution of 0.400 g (1.84 mmol) tert-butylindole-5-carboxylate in 15 ml absolute DMF and stirred at room temperature for one hour. A solution of 0.483 g (1.84 mmol) 2-(4-octyl-phenoxymethyl)oxirane in 15 ml absolute DMF is added drop-wise. Following four hours of heating at 60° C. and subsequent cooling, hydrolysis is carried out in a semi-saturated NaCl solution. Four extractions with diethyl ether, combination of the organic phases, concentration to half the volume on the rotary evaporator, three wash steps with saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a yellow oil which is purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 90:10) and yields the product as a colorless oil.

1. stirringstirred at room temperature for one hour
2. waitFollowing four hours
3. temperatureof heating at 60° C.
4. customsubsequent cooling, hydrolysis
5. extractionFour extractions
6. concentrationwith diethyl ether, combination of the organic phases, concentration to half the volume
7. customon the rotary evaporator, three
8. washwash steps with saturated NaCl solution
9. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
10. customleave as a crude product a yellow oil which
11. customis purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 90:10)