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

HRID 734666노트

반응식

HRID 734666 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-aadf442793f448b2b104c75b573591ad
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592357B2

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