Acetic Acid → HCID 86755685, compound

HRID 1386612Notes

Reaction equation

HRID 1386612 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)(=O)[CH3:4].[C:25]([OH:28])(=[O:27])[CH3:26].O1CC[CH2:31][CH2:30]1>>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6](/[C:3](/[CH3:4])=[CH:26]/[C:25]([O:28][CH2:30][CH3:31])=[O:27])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11208635HCID 11208635, compound

Product 1

HCID 86755685HCID 86755685, compound

Procedure

To a suspension of sodium hydride (60% in oil, 0.37 g) in tetrahydrofuran (40 ml) was added by portions 4-acetyl-4′-n-heptylbiphenyl (2.50 g) at ambient temperature. After stirring at ambient temperature for 1 hours, to the solution was added triethyl phosphonoacetate (1.9 ml) and the mixture was heated to reflux for 5 hours. After cooling to ambient temperature, to the mixture was added acetic acid (0.53 ml) and evaporated. The residue was taken up into a mixture of water and ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (200 ml) eluting with mixture of n-hexane and diisopropyl ether (99:1-20:1, V/V) to give Ethyl (E)-3-[4-(4-heptylphenyl)phenyl]-2-butenoate (2.19 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling to ambient temperature, to the mixture
  4. customevaporated
  5. additionThe residue was taken up into a mixture of water and ethyl acetate
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel (200 ml)
  10. washeluting with mixture of n-hexane and diisopropyl ether (99:1-20:1, V/V)

Sources & evidence

ORD record
ord-a2517018ed9c4fb19f04eb85ba89bc1c
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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