Ethyl orthoformate → 3-(5-Formyl-4-methyl-1H-pyrrol-2-yl)propanoic acid

HRID 397432Notes

Reaction equation

HRID 397432 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[NH:10][C:9]([C:11](O)=[O:12])=[C:8]([CH3:14])[CH:7]=1)([OH:3])=[O:2].C(OCC)(OCC)OCC>O>[CH:11]([C:9]1[NH:10][C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])=[CH:7][C:8]=1[CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 22390964HCID 22390964, compound

Product 1

HCID 223909933-(5-Formyl-4-methyl-1H-pyrrol-2-yl)propanoic acidYield 100.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-(2-carboxy-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid (e.g, 6.59 mmol) in trfluoroacetic acid (6 mL) was stirred at room temperature for 10 minutes. It was then cooled to 0° C. and to it was added triethyl orthoformate (6 mL). The mixture was stirred at 0° C. for 10 minutes and at room temperature for 10 minutes. The reaction was poured into water (50 mL) and extracted with ethyl acetate. The extract was dried and concentrated to give 1.2 g of 3-(5-formyl-4-methyl-1H-pyrrol-2-yl)-propionic acid as a brown solid. 1H NMR (300 MHz, DMSO-d6) δ 12.17 (brs, 1H), 11.50 (brs, 1H), 9.44 (s, 1H, CHO), 5.85 (s, 1H), 2.74 (t, J=7.4 Hz, 2H, CH2), 2.54 (t, J=7.4 Hz, 2H, CH2, CH2), 2.23 (s, 3H, CH3). MS 182 [M++1].

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9678b8a953f74d3aa5857450da7ffae6
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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