Dimethylformamide → 3-Formyl-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro [3,2-b]-pyridin-2(4H)-one

HRID 552902Notes

Reaction equation

HRID 552902 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[Cl:11][C:12]1[N:17]=[CH:16][C:15]([CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH:21]3[O:25][C:26](=[O:28])[CH:27]=[C:20]23)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH:3]([C:27]1[C:26](=[O:28])[O:25][CH:21]2[CH2:22][CH2:23][CH2:24][N:19]([CH2:18][C:15]3[CH:16]=[N:17][C:12]([Cl:11])=[CH:13][CH:14]=3)[C:20]=12)=[O:4]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 167527744-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one

Product 1

HCID 577798293-Formyl-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro [3,2-b]-pyridin-2(4H)-one

Procedure

With ice-cooling, 1.89 ml (24.56 mmol) of N,N-dimethylformamide and 0.28 ml (3.02 mmol) of phosphoryl chloride are initially charged, and after one hour 500 mg (1.89 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one (1-2) are added. The mixture is then stirred at room temperature for two hours. The reaction mixture is then made alkaline using sodium carbonate, and the precipitated solid is filtered off and washed with water. This gives 0.33 g (56% of theory) of 3-formyl-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one.

Workup

  1. temperatureWith ice-cooling
  2. filtrationthe precipitated solid is filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-99351246fd6d4ed4a2159bafa5af4613
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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