Chloral → 1-Methyl-alpha-trichloromethylpyrrole-2-methanol

HRID 1732556Notes

Reaction equation

HRID 1732556 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[O:7]=[CH:8][C:9]([Cl:12])([Cl:11])[Cl:10].C(N(CC)CC)C>CCOCC.[Cl-].[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:8]([OH:7])[C:9]([Cl:12])([Cl:11])[Cl:10]

Participants

8

Reactant 3

HCID 6407ChloralHCID 73041-MethylpyrroleHCID 8471Triethylamine

Product 1

HCID 155715331-Methyl-alpha-trichloromethylpyrrole-2-methanolYield 105.5%

Reagents, catalysts & solvents 4

HCID 785HydroquinoneCatalystHCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of N-methylpyrrole (8.10 g, 0.1 mol) in ether (50 ml) was added a solution of chloral (16.21 g, 0.1 mol) in ether (50 ml). To this were added p-toluene-sulfonic acid (200 mg) and hydroquinone (5 mg). Then the mixture was refluxed for 15 hours. After adding triethylamine (5 ml), the mixture was stirred for 5 minutes. Brine (100 ml) was added and the organic layer separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine (100 ml). After drying over magnesium sulfate, the organic solution was filtered through a bed of activated charcoal, and concentration afforded the adduct 1-methyl-2-(2',2',2'-trichloro-1'-hydroxyethyl)pyrrole (24.1 g) as pale brown prisms.

Workup

  1. temperatureThen the mixture was refluxed for 15 hours
  2. customthe organic layer separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine (100 ml)
  5. dry with materialAfter drying over magnesium sulfate
  6. filtrationthe organic solution was filtered through a bed of activated charcoal, and concentration

Sources & evidence

ORD record
ord-de7142f51df74172a9254a2d1e36e00f
Source dataset
uspto-grants-1980_12
Patent number
US04238396

Reaction notes

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