Chlorotrimethylsilane → HCID 57423684, compound

HRID 1725168Notes

Reaction equation

HRID 1725168 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH2:20][C:21]([OH:23])=[O:22])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.Cl[Si](C)(C)[CH3:26]>CO>[CH3:26][O:23][C:21](=[O:22])[CH2:20][N:10]1[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:13]=[C:9]1[C:6]1[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 57423683HCID 57423683, compound

Product 1

HCID 57423684HCID 57423684, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To [2-(4-methoxy-phenyl)-5-phenyl-pyrrol-1-yl]-acetic acid (3.4 g, 11.0 mmol) dissolved in anhydrous MeOH (200 mL) and cooled to 0° C. is added chlorotrimethylsilane (1.40 mL, 11.0 mmol). The mixture is refluxed for ˜12 h. The contents are concentrated in vacuo. The crude product is purified by flash chromatography on silica gel (10% hexanes/ethyl acetate) to give-(2,5-Diphenyl-pyrrol-1-yl)-acetic acid methyl ester as a yellow solid (2.68 g), characterized by LCMS (Obs: 322.56, Cal: 321.14) and 1H NMR.

Workup

  1. temperatureThe mixture is refluxed for ˜12 h
  2. concentrationThe contents are concentrated in vacuo
  3. customThe crude product is purified by flash chromatography on silica gel (10% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-cbfbdc3fe71749cfa4ccbfe86374545f
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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