Dichloromethane → HCID 12897073, compound

HRID 1980930Notes

Reaction equation

HRID 1980930 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.C(Cl)Cl.[C:13]1([CH2:19][C:20](Cl)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[C:13]1([CH2:19][C:20]([C:5]2[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7679Phenylacetyl chlorideHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

HCID 12897073HCID 12897073, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen, methyl pyrrole-3-carboxylate (920 mg., 7 mmoles) was dissolved in 25 ml. of methylene chloride. Phenylacetyl chloride (930 mg., 6 mmoles) was added and dissolved. Finally, stannic chloride (1.2 ml., 12 mmoles) was added. The reaction mixture was stirred for 3 hours, water (15 ml.) added dropwise, diluted with 50 ml. of ether, the organic phase separated, washed with 20 ml. of water and evaporated to dryness to yield methyl 5-phenylacetylpyrrole-3-carboxylate (semisolid, Rf 0.3 on silica gel thin layer chromatography with ethyl acetate-1/hexane-5/5% acetic acid as eluant). The entire batch was employed without weight determination in the next step.

Workup

  1. dissolutiondissolved
  2. additiondiluted with 50 ml
  3. customof ether, the organic phase separated
  4. washwashed with 20 ml
  5. customof water and evaporated to dryness

Sources & evidence

ORD record
ord-3d56fcd6053f45d4b17ee0423843427d
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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