Formaldehyde → Methyl 2-[3-chloro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-propenoate

HRID 15124

反応式

HRID 15124 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:9][C:8]([O:17][CH3:18])=[CH:7][CH:6]=2.[C:19](=O)([O-])[O-].[K+].[K+].C=O.C(OCC)(=O)C>C1CCCCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12](=[CH2:19])[C:13]([O:15][CH3:16])=[O:14])=[N:9][C:8]([O:17][CH3:18])=[CH:7][CH:6]=2

参加物

8

反応物 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57707490Methyl [3-chloro-6-(methyloxy)-[1,5]naphthyridin-4-yl]acetate

生成物 1

HCID 57486868Methyl 2-[3-chloro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-propenoate収率 89%

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒HCID 8078Cyclohexane溶媒

反応条件

温度
80 °C

実験手順

To a solution of methyl [3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]acetate (43 g, 162 mmol) in cyclohexane (1060 ml) was added benzyltriethylammonium chloride (71.2 g, 313 mmol), potassium carbonate (42 g, 304 mmol) and paraformaldehyde (42 g). The reaction mixture was then heated at 80° C. for 24 hours, cooled and treated with ethyl acetate and water. The aqueous was extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed under reduced pressure. The residue was subjected to column chromatography on silica gel using a hexane and ethyl acetate gradient to provide the desired compound (40 g, 89%).

後処理

  1. temperaturecooled
  2. extractionThe aqueous was extracted with ethyl acetate
  3. customThe combined organic phases were dried
  4. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-6b4e56ec1d8f4d4cac9a4ee473daecdc
出典データセット
uspto-grants-2010_06
特許番号
US07732460B2

関連ノート

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