2-Propenoic acid, 3-phenyl-, methyl ester → Methyl 4-phenyl-1H-pyrrole-3-carboxylate

HRID 894067Notes

Reaction equation

HRID 894067 reaction equation
CC1C=CC(S([CH2:11][N:12]=[CH2:13])(=O)=O)=CC=1.[C:14]([O:24][CH3:25])(=[O:23])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O1CCCC1.[H-].[Na+]>O>[C:17]1([C:16]2[C:15]([C:14]([O:24][CH3:25])=[O:23])=[CH:11][NH:12][CH:13]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 562852HCID 562852, compound

Product 1

HCID 5142464Methyl 4-phenyl-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Tosylmethyl isocyanide (1 g., 5 mmoles) and methyl cinnamate (0.8 g., 5 mmoles) were combined in 50 ml. of tetrahydrofuran and dissolved by stirring at room temperature. The solution was cooled to -50° C. and sodium hydride (57% dispersion in oil, 210 mg., 5 mmoles) added. After stirring for 15 minutes at -50° C., the reaction was warmed to room temperature and stirred for approximately 16 hours. Water (20 ml.) was added and the product extracted into 35 ml. ether. The ether was back-washed with 20 ml. of water, evaporated to dryness, the residue triturated with ether and methyl 4-phenylpyrrole-3-carboxylate (230 mg., m.p. 182°-185° C., m/e 201) recovered by filtration. The product was recrystallized from acetone/hexane (210 mg., m.p. 184°-187° C.).

Workup

  1. temperatureThe solution was cooled to -50° C.
  2. stirringAfter stirring for 15 minutes at -50° C.
  3. temperaturethe reaction was warmed to room temperature
  4. stirringstirred for approximately 16 hours
  5. extractionthe product extracted into 35 ml
  6. washThe ether was back-washed with 20 ml
  7. customof water, evaporated to dryness
  8. customthe residue triturated with ether and methyl 4-phenylpyrrole-3-carboxylate (230 mg., m.p. 182°-185° C., m/e 201)
  9. filtrationrecovered by filtration
  10. customThe product was recrystallized from acetone/hexane (210 mg., m.p. 184°-187° C.)

Sources & evidence

ORD record
ord-8d32aa80ec4448aa986a0c405f07819b
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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