反应详情

5.33 g (52.2 mmol) acetic anhydride are mixed with 30 ml absolute DMSO, stirred at room temperature for 10 min and added drop-wise to a solution of 0.626 g (1.31 mmol) tert-butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]indole-5-carboxylate in 20 ml absolute DMSO. Having stirred for 17 hours, the solution is poured into a mixture of 5% sodium hydrogen carbonate solution and saturated NaCl solution (1:1, v/v) and hydrolyzed for 10 min. Four extractions using 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 95:5) and yields the product as a colorless oil.

1. stirringHaving stirred for 17 hours
2. waitv/v) and hydrolyzed for 10 min
3. extractionFour extractions
4. concentrationdiethyl ether, combination of the organic phases, concentration to half the volume
5. customon the rotary evaporator, three
6. washwash steps with saturated NaCl solution
7. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
8. customleave as a crude product a yellow oil which
9. customis purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 95:5)