Chloromethyl ethyl ether → Diethyl 1-(ethoxymethyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate

HRID 880440Notes

Reaction equation

HRID 880440 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].[CH2:29]([O:31][CH2:32]Cl)[CH3:30]>CS(C)=O>[CH2:29]([O:31][CH2:32][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])[CH3:30]

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 291171diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4-dicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 66914830Diethyl 1-(ethoxymethyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium tert-butoxide (557 mg, 4.97 mmol) was added to a stirred solution of diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4-dicarboxylate (600 mg, 1.99 mmol) in dimethylsulfoxide (15 mL) at 10° C. and stirred at ambient temperature for 1 h. Upon cooling to 10° C., chloromethyl ethyl ether (377 mg, 3.99 mmol) was added and stirred 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 8% ethyl acetate in petroleum ether as eluent to afford diethyl 1-(ethoxymethyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate (400 mg, 56%) as a liquid.

Workup

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

Sources & evidence

ORD record
ord-b21a96e7296c4907bed671e2a4a2927d
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

Loading…