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

HRID 880441Notes

Reaction equation

HRID 880441 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[NH:12][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].Br[CH2:30][CH2:31][CH2:32][OH:33]>CS(C)=O>[OH:33][CH2:32][CH2:31][CH2:30][N:12]1[C:8]([CH3:7])=[C:9]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 291171diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4-dicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67240867Diethyl 1-(3-hydroxypropyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylateYield 83.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-de0066dd60fe4af4adc892e2d95336f6
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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