Ethyl orthoformate → HCID 22561750, compound

HRID 1839671Notes

Reaction equation

HRID 1839671 reaction equation
C([O:8][CH2:9][CH3:10])(OCC)OCC.[CH3:11][C:12]1[NH:13][CH:14]=[C:15](C)[C:16]=1[C:17]1[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH:22]=1>C(O)(C(F)(F)F)=O>[CH3:14][C:15]1[C:16]([C:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH:18]=2)=[C:12]([CH3:11])[NH:13][C:10]=1[CH:9]=[O:8]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 22561850HCID 22561850, compound

Product 1

HCID 22561750HCID 22561750, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

Triethyl orthoformate (6 mL) was added to a solution of 4-(2,4-dimethyl-1H-pyrrol-3-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine (360 mg) in TFA (6 mL) at 0° C. The mixture was stirred at 0° C. for 10 mins and then at rt for 40 mins. The solvent was removed and to the residue was added NaHCO3, extracted with ethyl acetate, dried and concentrated to give 356 mg of 3,5-dimethyl-4-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-pyrrole-2-carbaldehyde.

Workup

  1. waitat rt for 40 mins
  2. customThe solvent was removed and to the residue
  3. additionwas added NaHCO3
  4. extractionextracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a016b98a4f1440dc829e0da09f0cd33c
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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