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

HRID 552902노트

반응식

HRID 552902 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-99351246fd6d4ed4a2159bafa5af4613
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951951B2

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