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

HRID 1732559Notes

Reaction equation

HRID 1732559 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>[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 6407ChloralHCID 73041-MethylpyrroleHCID 8471Triethylamine

Product 1

HCID 155715331-Methyl-alpha-trichloromethylpyrrole-2-methanolYield 102.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of N-methylpyrrole (1.62 g, 20 mmol) in ether (10 ml) was added a solution of chloral (3.24 g, 22 mmol) in ether (10 ml). To this was added Amberlyst (160 mg) and the mixture was stirred under reflux for 18 hours. After cooling to room temperature and adding triethylamine (0.3 ml), the mixture was stirred for 5 minutes and filtered through a layer of Celite. The filtrate was concentrated under reduced pressure to afford the crude adduct 1-methyl-2-(2',2',2'-trichloro-1'-hydroxyethyl)pyrrole (4.68 g) as pale brown prisms.

Workup

  1. additionTo this was added Amberlyst (160 mg)
  2. temperatureunder reflux for 18 hours
  3. stirringthe mixture was stirred for 5 minutes
  4. filtrationfiltered through a layer of Celite
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ccc778a369e438d93794ce85f201c29
Source dataset
uspto-grants-1980_12
Patent number
US04238396

Reaction notes

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