1-Methyl-1H-pyrrole-2-carbaldehyde → Methyl (2-(1-methyl-2-pyrrolyl)-6-benzoxazolyl)acetate

HRID 1372748Notes

Reaction equation

HRID 1372748 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]=[O:8].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:12][C:11]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[O:8][C:11]2[CH:12]=[C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:15][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 145041-Methyl-1H-pyrrole-2-carbaldehydeHCID 12217721Iodo benzene diacetateHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

Product 1

HCID 58778961Methyl (2-(1-methyl-2-pyrrolyl)-6-benzoxazolyl)acetateYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (10 ml), 1-methylpyrrole-2-carbaldehyde (0.33 ml, 3.09 mmol) and methyl 4-amino-3-hydroxyphenylacetate (559 mg, 3.09 mmol) were stirred for 4 hours at room temperature. Iodobenzene diacetate (1.19 g, 3.70 mmol) was added to the reaction mixture. After stirring at room temperature for 30 minutes, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (3:1, v/v) eluate fractions, methyl (2-(1-methyl-2-pyrrolyl)-6-benzoxazolyl)acetate (228 mg, 27%) was obtained as a yellow solid.

Workup

  1. distillationthe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (3:1

Sources & evidence

ORD record
ord-c5c7f958390d471fab1bd96cf254d830
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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