Toluene → 2-(4-Benzyloxyphenyl)-5-methyl-1-(4-pentylcyclohexylmethyl)-1H-pyrrole

HRID 1072752Notes

Reaction equation

HRID 1072752 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.C(C1CCC(CC[NH2:35])CC1)CCCC.O.[C:37]1([CH3:47])[CH:42]=[CH:41][C:40](S(O)(=O)=O)=[CH:39][CH:38]=1.[C:48]1(C)C=[CH:52][CH:51]=[CH:50][CH:49]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:35]([CH2:47][CH:37]3[CH2:42][CH2:41][CH:40]([CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH2:39][CH2:38]3)[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 4

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 223875251-(4-Benzyloxyphenyl)-1,4-pentanedioneHCID 223875482-((1s,4r)-4-Pentylcyclohexyl)ethanamine

Product 1

HCID 223876002-(4-Benzyloxyphenyl)-5-methyl-1-(4-pentylcyclohexylmethyl)-1H-pyrroleYield 25.3%

Procedure

A solution of 1-(4-benzyloxyphenyl)pentane-1,4-dione (2.00 g, 7.08 mmol), 2-(4-pentylcyclohexyl)ethylamine (1.30 g, 7.08 mmol) and p-toluenesulfonic acid monohydrate (101 mg, 0.523 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=30:1) to give the object compound as an oily substance. 770 mg (yield: 25.3%)

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=30:1)
  4. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-a2cdf2d7cb9f479c847af7f52cf450d2
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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