Water → HCID 22561880, compound

HRID 983074Notes

Reaction equation

HRID 983074 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[C:4]([CH2:7][C:8]([OH:10])=[O:9])[CH:3]=1.[CH:11](OCC)(OCC)[O:12]CC.O>C(O)(C(F)(F)F)=O>[CH:11]([C:5]1[NH:6][C:2]([CH3:1])=[CH:3][C:4]=1[CH2:7][C:8]([OH:10])=[O:9])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 31214Ethyl orthoformateHCID 22561983102074-66-8

Product 1

HCID 22561880HCID 22561880, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (5-methyl-1H-pyrrol-3-yl)-acetic acid (8.2 mmol) in TFA (6 mL) at 0° C. was added triethyl orthoformate (6 mL), it was then at 0° C. for 10 mins and at rt for 0.5 hours. The reaction was poured into water, extracted with ethyl acetate, dried and concentrated. The residue was purified on a silica gel column to give 1.15 g (84%) of (2-formyl-5-methyl-1H-pyrrol-3-yl) acetic acid.

Workup

  1. waitat rt for 0.5 hours
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-29b9a51f38b94d8abc187be66ef61641
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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