Hydrochloric Acid → Ethyl 7-(4-methoxyphenyl)-4,7-dioxoheptanoate

HRID 2362223Notes

Reaction equation

HRID 2362223 reaction equation
[O:1]1C=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9].Cl.[C:19]([O-:22])([O-])=[O:20].[Na+].[Na+].[CH2:25](O)[CH3:26]>>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:8](=[O:9])[CH2:7][CH2:6][C:2](=[O:1])[CH2:3][CH2:4][C:19]([O:22][CH2:25][CH3:26])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 2440833-(furan-2-yl)-1-(4-methoxyphenyl)prop-2-en-1-one

Product 1

HCID 58297647Ethyl 7-(4-methoxyphenyl)-4,7-dioxoheptanoateYield 49%

Procedure

To a solution of compound 3-(furan-2-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (8.0 g, 35.1 mmol) in ethanol (150 mL) was added conc. HCl (38.0 mL). The resulting mixture was refluxed for 14 h. Then the solution was neutralized with 10% Na2CO3 solution. The volatile was removed. The residue was diluted with DCM (750 mL), washed with water (200 mL) and brine (200 mL), dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (PE:EA=8:1˜4:1) to give ethyl 7-(4-methoxyphenyl)-4,7-dioxoheptanoate (25C) as a yellow solid (5.10 g, 49%).

Workup

  1. temperatureThe resulting mixture was refluxed for 14 h
  2. customThe volatile was removed
  3. additionThe residue was diluted with DCM (750 mL)
  4. washwashed with water (200 mL) and brine (200 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (PE:EA=8:1˜4:1)

Sources & evidence

ORD record
ord-ccfb320bbee748abb54917aae327b17a
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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