Sulfuric Acid → methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl)propanoate

HRID 477505

반응식

HRID 477505 반응식
[OH:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[CH2:7][C:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])([CH3:10])[O:9][C:4]=2[C:3]=1[CH2:19][CH2:20][CH3:21].[CH3:22]OC(OC)OC.S(=O)(=O)(O)O>>[OH:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[CH2:7][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:22])=[O:14])([CH3:10])[O:9][C:4]=2[C:3]=1[CH2:19][CH2:20][CH3:21]

참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 139207383-(3,4-dihydro-7-hydroxy-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl)propanoic acid

생성물 1

HCID 2801556methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl)propanoate

실험 절차

A mixture of the title compound of Example 3 (4.3 g, 14.7 mmole), 6 ml of trimethylorthoformate, and 1.4 ml of sulfuric acid was stirred at room temperature for two hours. The reaction mixture was poured onto stirred ice/water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, and concentrated to an oil. The oil was purified by chromatography on silica gel, giving 3.7 g of the title compound as a crystalline solid, m.p. 101.5°-102.5°. Structure assignment was consistent with nmr and infrared spectra. ##STR7##

후처리

  1. additionThe reaction mixture was poured
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to an oil
  6. customThe oil was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-522ab0b872744ce4bf0277c64cde7da1
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04888356

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