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

HRID 1732555Notes

Reaction equation

HRID 1732555 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].O>C1C=CC=CC=1>[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

5

Reactant 3

HCID 962WaterHCID 6407ChloralHCID 73041-Methylpyrrole

Product 1

HCID 155715331-Methyl-alpha-trichloromethylpyrrole-2-methanolYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of N-methylpyrrole (810 mg, 10 mmol) dissolved in benzene (10ml) was added dropwise a solution of chloral (1.47 g, 10 mmol) dissolved in benzene (5 ml) under ice-cooling for 40 minutes. After the mixture was stirred for 1 hour at room temperature, water was added thereto and the mixture was extracted with ether. The extract was dried over sodium sulfate and concentrated to afford 1-methyl-2-(2',2',2'-trichloro-1'-hydroxyethyl)pyrrole (2.04 g) as an oil.

Workup

  1. temperaturecooling for 40 minutes
  2. extractionthe mixture was extracted with ether
  3. dry with materialThe extract was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dee83c6b791f4a0dbfada5317bd2bcba
Source dataset
uspto-grants-1980_12
Patent number
US04238396

Reaction notes

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