Dimethylformamide → HCID 86626938, compound

HRID 1514647Notes

Reaction equation

HRID 1514647 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[C:11]([C:15]1[N:19]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([CH3:28])=[C:17]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:16]=1)([CH3:14])([CH3:13])[CH3:12]>O>[C:11]([C:15]1[N:19]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([CH3:28])=[C:17]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:16]=1[CH:8]=[O:9])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 66670270HCID 66670270, compound

Product 1

HCID 86626938HCID 86626938, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, 0.72 ml of phosphorus oxychloride was added to 4 ml of N,N-dimethylformamide at an inner temperature of from 10 to 20° C., followed by stirring at room temperature for 15 minutes. A 5 ml portion of N,N-dimethylformamide solution of 2.00 g ethyl 5-tert-butyl-2-methyl-1-(2-phenylethyl)-1H-pyrrole-3-carboxylate was added to this solution under ice-cooling at an inner temperature of from 10 to 20° C., followed by stirring overnight at 60° C. Water was added at 0° C., pH was adjusted to 8 with potassium carbonate, and extraction was carried out with diethyl ether. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. Then, the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:8-1:7) to obtain 1.63 g of ethyl 5-tert-butyl-4-formyl-2-methyl-1-(2-phenylethyl)-1H-pyrrole-3-carboxylate as a light yellow solid.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooling at an inner temperature of from 10 to 20° C.
  3. stirringby stirring overnight at 60° C
  4. extractionpH was adjusted to 8 with potassium carbonate, and extraction
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThen, the solvent was evaporated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:8-1:7)

Sources & evidence

ORD record
ord-a8ee83fe8685472d9faada6ceae4f07a
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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