Acetic Acid → Ethyl 3-[1-hydroxy-4-(4-ethoxycarbonylbutoxy)benzen-2-yl]prop-2E-enoate

HRID 465955Notes

Reaction equation

HRID 465955 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[O:19][C:18](=[O:23])[CH:17]=[CH:16]2)=[O:7])[CH3:4].[C:24](O)(=O)[CH3:25].C([OH:30])C>>[OH:19][C:20]1[CH:21]=[CH:22][C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]([O:5][CH2:3][CH3:4])=[O:7])=[CH:14][C:15]=1/[CH:16]=[CH:17]/[C:18]([O:23][CH2:24][CH3:25])=[O:30]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 702Ethanol2×HCID 24758Sodium hydrideHCID 150296966-(4-Ethoxycarbonylbutyl)oxycoumarin

Product 1

HCID 19598049Ethyl 3-[1-hydroxy-4-(4-ethoxycarbonylbutoxy)benzen-2-yl]prop-2E-enoate

Procedure

Sodium hydride (content: 62%; 60 mg) was gradually added to anhydrous ethanol (10 ml) and dissolved. A solution of the ester (314 mg; prepared in reference example 26) in anhydrous ethanol. (1 ml) was added to the solution. The mixture was stirred for 4 hr. at 70° C. and then for 30 min at 80° C. Glacial acetic acid (210 mg) was added to the reaction solution with ice-cooling to stop the reaction. The solvent was removed from the reaction solution under reduced pressure. The residue was diluted with ether. The mixture was washed with water. Aqueous layer was removed. Ethereal layer was dried over anhydrous magnesium sulfate and then evaporated. The residue was purified by column chromatography on silica gel (n-hexane: ethyl acetate=2:1) to give the title compound (122 mg) having the following physical data.

Workup

  1. dissolutiondissolved
  2. addition(1 ml) was added to the solution
  3. waitat 70° C. and then for 30 min at 80° C
  4. temperaturecooling
  5. customthe reaction
  6. customThe solvent was removed from the reaction solution under reduced pressure
  7. additionThe residue was diluted with ether
  8. washThe mixture was washed with water
  9. customAqueous layer was removed
  10. dry with materialEthereal layer was dried over anhydrous magnesium sulfate
  11. customevaporated
  12. customThe residue was purified by column chromatography on silica gel (n-hexane: ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b5ac42661b5d4fe2a999f75c4f8d9bba
Source dataset
uspto-grants-1992_10
Patent number
US05155104

Reaction notes

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