Ethyl orthoformate → HCID 22561687, compound

HRID 1839672Notes

Reaction equation

HRID 1839672 reaction equation
[CH3:1][C:2]1[C:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)=[C:5]([CH3:14])[NH:4][C:3]=1[C:15](O)=[O:16].C(OCC)(OCC)OCC>C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[C:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)=[C:5]([CH3:14])[NH:4][C:3]=1[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 22561810HCID 22561810, compound

Product 1

HCID 22561687HCID 22561687, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3,5-dimethyl-4-(1-methyl-piperidin-4-yl)-1H-pyrrole-2-carboxylic acid (12.67 mmol) in TFA (75 mL) was stirred at 0° C. for 30 mins. To the mixture was added triethyl orthoformate (20 mL), it was then allowed to warm up slowly to rt for 2 hours. The solvent was removed and to the residue was added NaHCO3, extracted with ethyl acetate, dried and concentrated to give 2.56 g of 3,5-dimethyl-4-(1-methyl-piperidin-4-yl)-1H-pyrrole-2-carbaldehyde as a light yellow solid.

Workup

  1. customThe solvent was removed and to the residue
  2. additionwas added NaHCO3
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-571de86a70e747e5a8d0a3b980962bdb
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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