Ethanolamine → 2-(2-Ethyl-5-phenyl-1H-pyrrol-1-yl)ethanol

HRID 1510964Notes

Reaction equation

HRID 1510964 reaction equation
[C:1]1([C:7](=O)[CH2:8][CH2:9][C:10](=O)[CH2:11][CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([CH2:17][NH2:18])[OH:16].C(O)(=O)C(C)(C)C.CCCCCCC.O1CCCC1.C1(C)C=CC=CC=1>ClCCl.O>[OH:16][CH2:15][CH2:17][N:18]1[C:10]([CH2:11][CH3:12])=[CH:9][CH:8]=[C:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 700EthanolamineHCID 6417Pivalic acidHCID 110632161-Phenyl-1,4-hexanedioneHCID 22168748HCID 22168748, compound

Product 1

HCID 221687532-(2-Ethyl-5-phenyl-1H-pyrrol-1-yl)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 1-phenyl-hexane-1,4-dione (5 g), ethanol amine (1.6 g) and pivalic acid (2.15 g) in a solvent mixture containing n-heptane:tetrahydrofuran:toluene (4:1:1, 50 mL) was refluxed with stirring at 110-120° C. Water formed during the reaction was removed azeotropically during 3 to 4 hrs. The reaction mixture was cooled and the solvent was removed. The residue obtained was dissolved in dichloromethane (50 mL), washed with saturated sodium bicarbonate solution (50 mL), water (50 mL), and then with brine (50 mL), dried (Na2SO4) and the solvent was evaporated. The crude compound obtained as an oily mass. The crude substance was used in the next step without purification.

Workup

  1. temperaturewas refluxed
  2. customwas removed azeotropically during 3 to 4 hrs
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was removed
  5. customThe residue obtained
  6. washwashed with saturated sodium bicarbonate solution (50 mL), water (50 mL)
  7. dry with materialwith brine (50 mL), dried (Na2SO4)
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9391d75e98a54d20bc0ab209b57a0245
Source dataset
uspto-grants-2012_07
Patent number
US08212057B2

Reaction notes

Loading…