Dimethylformamide → HCID 20740433, compound

HRID 1883191Notes

Reaction equation

HRID 1883191 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[CH2:11]([N:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:20])[CH:12]=[CH2:13].C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1.O.C1COCC1>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([C:19]([C:15]2[N:14]([CH2:11][CH:12]=[CH2:13])[CH:18]=[C:17]([CH:4]=[O:5])[CH:16]=2)=[O:20])=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 23510369(4-Methoxyphenyl)[1-(prop-2-en-1-yl)-1H-pyrrol-2-yl]methanone

Product 1

HCID 20740433HCID 20740433, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, to a solution of the compound of Reference Example 5-2 (5 g) in THF (15 mL) was added KOtBu (3.07 g). Further, a solution of allyl bromide (4.51 g) in THF (9.0 mL) was added thereto, and the mixture was stirred at 45° C. for 2 hours. Water was added to the mixture, and the mixture was extracted twice with toluene. The organic layers were concentrated to give [1-(2-propenyl)-1H-pyrrol-2-yl][4-methoxyphenyl]ketone (6.00 g, 98%). To DMF (7.31 g) was added dropwise POCl3 (11.5 g) at 10° C., and the mixture was stirred for 15 minutes. To the mixture was added THF (5.41 g), and thereto was added dropise a solution of [1-(2-propenyl)-1H-pyrrol-2-yl][4-methoxyphenyl]ketone in toluene (10 mL). The mixture was stirred at room temperature for 5 hours, and thereto was added a solution of sodium acetate (11.2 g) in water (22 g), and the mixture was stirred for 3 hours. The precipitated crystals were collected by filtration, and dried to give (4-formyl-1-(2-propenyl)-1H-pyrrol-2-yl) (4-methoxyphenyl) ketone (3.31 g). The organic layer of the filtrate was collected, concentraed, and the precipitated crystals were collected by filtration, and dried (1.48 g, total 4.79 g, 71%).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. stirringthe mixture was stirred for 3 hours
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-14613fd614894cb6bffd058b1474b725
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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