3-(3,4-Dihydroxyphenyl)Prop-2-Enoic Acid → 2-(3,4-dihydroxycinnamoyl) oxymethyl-5-hydroxy-4H-pyran-4-one

HRID 375698

반응식

HRID 375698 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[OH-].[Na+].CN(C)C=O.[CH:21]1[C:26](=[O:27])[C:25]([OH:28])=[CH:24][O:23][C:22]=1[CH2:29]Cl>CO.C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:5]=[CH:6][C:7]([O:9][CH2:29][C:22]1[O:23][CH:24]=[C:25]([OH:28])[C:26](=[O:27])[CH:21]=1)=[O:8]

참가 물질

7

반응물 4

HCID 25183-(3,4-Dihydroxyphenyl)Prop-2-Enoic AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 82051Chlorokojic acid

생성물 1

HCID 541328622-(3,4-dihydroxycinnamoyl) oxymethyl-5-hydroxy-4H-pyran-4-one수율 53.6%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

0.81 g(4.5 mmol) of 3,4-dihydroxycinnamic acid and 0.18 g (4.5 mmol) of sodium hydroxide were dissolved into 40 ml of methanol. Residues obtained after distillating in methanol dissolved into 70 ml of N,N-dimethylformamide and 0.65 g (4.05 mmol) of chlorokojic acid prepared in the Reference Example was added thereto. The resulting mixture was heated with stirring for 2 hours in an oil bath of 110° C. After distillating the solvent, the residue was dissolved in 300 ml of ethyl acetate. The ethyl acetate solution was washed with 5% hydrochloric acid and distilled water, dried over magnesium sulfate, decolored with active charcoal and filtered. The filtrate was concentrated to give 0.66 g(48.8%) of 2-(3,4-dihydroxycinnamoyl) oxymethyl-5-hydroxy-4H-pyran-4-one as a solid.

후처리

  1. customResidues obtained
  2. additionwas added
  3. temperatureThe resulting mixture was heated
  4. washThe ethyl acetate solution was washed with 5% hydrochloric acid
  5. distillationdistilled water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-968d7c5522eb4facb2fa62d9db9429ea
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05486624

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