3-Amino-1-propanol → 3-[2-(4-Benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propan-1-ol

HRID 1072744Notes

Reaction equation

HRID 1072744 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][CH2:17][C:18](=O)[CH3:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][CH2:23][CH2:24][CH2:25][OH:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:22]([CH2:23][CH2:24][CH2:25][OH:26])[C:18]([CH3:19])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 223875251-(4-Benzyloxyphenyl)-1,4-pentanedione

Product 1

HCID 223873173-[2-(4-Benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propan-1-olYield 79.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(4-benzyloxyphenyl)pentan-1,4-dione (5.00 g, 17.7 mmol), 3-amino-1-propanol (1.33 g, 17.7 mmol) and p-toluenesulfonic acid monohydrate (253 mg, 1.33 mmol) in toluene (100 ml) was refluxed for 12 hours under heating using Dean-Stark's apparatus, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the object compound as a solid. 4.50 g (yield: 79.1%)

Workup

  1. temperatureunder heating
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-19c630a3a3744be5b050ebe4cdf2106b
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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