3-Bromo-1-propanol → Diethyl 1-(3-hydroxypropyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate

Potassium tert-butoxide (744 mg, 6.64 mmol) was added to a stirred solution of diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4 dicarboxylate (1.00 g, 1.99 mmol) in dimethylsulfoxide (15 mL) at 10° C. and stirred at ambient temperature for 1 h. The mixture was cooled to 10° C., 3-bromo-1-propanol (738 mg, 5.31 mmol) added and stirring continued at ambient temperature for 12 h. The mixture was poured onto ice-water and extracted with diethyl ether (5×10 mL). The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate and filtered. The filtrate was concentrated in vacuo and subjected to column chromatography over silica gel (100-200 mesh) using 40% of ethyl acetate in petroleum ether as eluent to afford of diethyl 1-(3-hydroxypropyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate (600 mg, 50%) as a liquid.

1. temperatureThe mixture was cooled to 10° C.
2. stirringstirring
3. waitcontinued at ambient temperature for 12 h
4. additionThe mixture was poured onto ice-water
5. extractionextracted with diethyl ether (5×10 mL)
6. washThe combined organic layers were washed with water, brine
7. dry with materialdried over anhydrous sodium sulphate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-de0066dd60fe4af4adc892e2d95336f6

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993574B2