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

HRID 552902ノート

反応式

HRID 552902 の反応式
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]

参加物

5

反応物 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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-99351246fd6d4ed4a2159bafa5af4613
出典データセット
uspto-grants-2011_05
特許番号
US07951951B2

反応ノート

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