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

HRID 1072192Notes

Reaction equation

HRID 1072192 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>FC(F)(F)C(O)=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

5

Reactant 3

HCID 962WaterHCID 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 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-(2-carboxy-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid (1.3 g, 6.59 mmol) in trifluoroacetic 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 (br s, 1H), 11.50 (br s, 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), 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-9b65b88ab32e497b9a36ff24a2f91519
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Reaction notes

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