Dimethylformamide → HCID 54105048, compound

HRID 1107831Notes

Reaction equation

HRID 1107831 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[CH2:11]([N:15]1[C:19]([C:20](=O)[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:18][C:17]([CH3:31])=[C:16]1[CH3:32])[CH:12]=[CH:13][CH3:14].[OH-].[Na+]>ClCCl>[CH2:11]([N:15]1[C:16]([CH3:32])=[C:17]([CH3:31])[C:18]([CH:8]=[O:9])=[C:19]1[C:20]([Cl:3])=[CH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH:12]=[CH:13][CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 54041294HCID 54041294, compound

Product 1

HCID 54105048HCID 54105048, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.38 ml (0.00408 mole) of phosphorus oxychloride was added to 0.29 g (0.00397 mole) of dry dimethylformamide and the mixture was stirred at room temperature for 30 minutes. A solution of 0.89g (0.00297 mole) of 1-(2-butenyl)-5-[3-(4-fluorophenyl)propionyl]-2,3-dimethylpyrrole in 4 ml of dichloromethane was added dropwise to the mixture and stirred at room temperature for 30 minutes. The reaction mixture was poured into ice-water and neutralized with an aqueous solution of sodium hydroxide. The aqueous mixture was extracted with 50 ml each of dichloromethane for three times. The extract was washed with 30 ml of a saturated aqueous solution of sodium hydrogencarbonate and 30 ml of a saturated aqueous solution of sodium chloride in turn and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography through silica gel using a 1:12 to 1:9 mixture of ethyl acetate and hexane as an eluent to give 0.41 g of the title compound (cis/trans=22/78) as a yellow oil.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. extractionThe aqueous mixture was extracted with 50 ml each of dichloromethane for three times
  3. washThe extract was washed with 30 ml of a saturated aqueous solution of sodium hydrogencarbonate and 30 ml of a saturated aqueous solution of sodium chloride in turn
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography through silica gel using a 1:12
  7. additionto 1:9 mixture of ethyl acetate and hexane as an eluent

Sources & evidence

ORD record
ord-03b1696b8355495baff090eaf076fe8f
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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