p-Toluenesulfonic acid → [2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester

HRID 1265290Notes

Reaction equation

HRID 1265290 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:27][Si:28]([CH3:37])([CH3:36])[CH2:29][CH2:30][O:31][C:32]([NH:34][NH2:35])=[O:33].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:27][Si:28]([CH3:37])([CH3:36])[CH2:29][CH2:30][O:31][C:32](=[O:33])[NH:34][N:35]1[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[CH:12][CH:13]=[C:14]1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10241327Hydrazinecarboxylic acid 2-trimethylsilanyl-ethyl esterHCID 112681471,4-Bis-(4-tert-butyl-phenyl)-butane-1,4-dione

Product 1

HCID 59050403[2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,4-bis-(4-tert-butyl-phenyl)-butane-1,4-dione (377 mg, 1.08 mmol) in toluene (3 mL) was treated with hydrazinecarboxylic acid 2-trimethylsilanyl-ethyl ester (212 mg, 1.18 mmol) and p-toluene sulfonic acid (11.3 mg). The resulting solution was heated to reflux under Ar for 1.5 h, then cooled to rt and concentrated in vacuo to provide crude [2,5-Bis-(4-tert-butyl-phenyl)-pyrrol-1-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester. The residue was not purified, but was deprotected immediately as follows.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux under Ar for 1.5 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd9bdd155c5245debe2ee59b025037b6
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Reaction notes

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