4-Chlorobenzaldehyde → Methyl 4-(4-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate

HRID 734666ノート

反応式

HRID 734666 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]1(C)[O:16]C(=O)CC(=O)O1.[C:20]([O:26][CH3:27])(=[O:25])[CH2:21][C:22]([CH3:24])=O.C([O-])(=O)C.[NH4+:32].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[CH2:10][C:11](=[O:16])[NH:32][C:22]([CH3:24])=[C:21]2[C:20]([O:26][CH3:27])=[O:25])=[CH:4][CH:3]=1

参加物

9

反応物 5

HCID 77264-ChlorobenzaldehydeHCID 7757Methyl acetoacetateHCID 11430Potassium CarbonateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 517165Ammonium Acetate

生成物 1

HCID 2849828Methyl 4-(4-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate収率 28.3%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Chlorobenzaldehyde (1.30 g, 9.30 mmol, 1.00 equiv), 2,2-dimethyl-1,3-dioxane-4,6-dione (1.34 g, 9.30 mmol, 1.00 equiv), methyl acetoacetate (1.00 mL, 9.30 mmol, 1.00 equiv), and ammonium acetate (0.752 g, 9.77 mmol, 1.05 equiv) were dissolved in acetic acid (10 mL) and heated to reflux for 2 hours. The reaction mixture was cooled to room temperature, neutralized with solid K2CO3, and diluted with EtOAc and water. The phases were separated, and the organic phase was washed with satd. NaCl. The organic phase was dried over Na2SO4, filtered and concentrated en vacuo to a yellow residue. Recrystallization (CH2Cl2/hexanes) provided 735 mg (28%) of the product as a pale yellow solid. MS (ES+) m/e 280 [M+H]+.

後処理

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customThe phases were separated
  4. washthe organic phase was washed with satd
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated en vacuo to a yellow residue
  8. customRecrystallization (CH2Cl2/hexanes)

出典と根拠

ORDレコード
ord-aadf442793f448b2b104c75b573591ad
出典データセット
uspto-grants-2009_09
特許番号
US07592357B2

反応ノート

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