Ethanolamine → 1-(2-Hydroxyethyl)-2,5-dimethylpyrrole

HRID 1906483Notes

Reaction equation

HRID 1906483 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[CH3:5][C:6](=O)[CH2:7][CH2:8][C:9](=O)[CH3:10]>C1(C)C=CC=CC=1>[OH:4][CH2:3][CH2:2][N:1]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]1[CH3:5]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 80352,5-Hexanedione

Product 1

HCID 959631-(2-Hydroxyethyl)-2,5-dimethylpyrroleYield 87.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 20 g (0.33 mol) of 2-aminoethanol and 38 g (0.33 mol) of 2,5-hexanedione was stirred until the vigorous reaction subsided. 100 ml of toluene was added and the solution was refluxed to 15 hours in a Dean-Stark apparatus. The solvent was removed in vacuo and the resulting oil was kugelrohr distilled at 110° C./1.5 mm to yield 40 g (87%) of a white solid. NMR: (CDCl3) δ 2.1 (1H, s), 2.2 (6H, s), 3.7 (4H, m), 5.6 (2H, s).

Workup

  1. temperaturethe solution was refluxed to 15 hours in a Dean-Stark apparatus
  2. customThe solvent was removed in vacuo
  3. distillationthe resulting oil was kugelrohr distilled at 110° C./1.5 mm

Sources & evidence

ORD record
ord-fa3b1c34e9a1468fb608aedcce512dad
Source dataset
uspto-grants-1987_03
Patent number
US04652573

Reaction notes

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