Water → HCID 54373732, compound

HRID 1600856Notes

Reaction equation

HRID 1600856 reaction equation
[H-].[Na+].[CH2:3]1[O:7][C:6]2[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:5]=2[O:4]1.[CH2:13]([O:15][C:16](=[O:37])[C:17]1[C:22]([O:23][C:24]2[CH:29]=[CH:28][C:27]3[O:30][CH2:31][O:32][C:26]=3[C:25]=2C=CC)=[CH:21][CH:20]=[CH:19][C:18]=1F)[CH3:14].O.[CH2:39]1[CH2:43]OC[CH2:40]1>CS(C)=O.C(OCC)(=O)C>[CH2:31]1[O:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([O:12][C:9]4[CH:8]=[C:6]5[O:7][CH2:3][O:4][C:5]5=[CH:11][C:10]=4[CH:40]=[CH:39][CH3:43])[C:17]=3[C:16]([O:15][CH2:13][CH3:14])=[O:37])=[CH:25][C:26]=2[O:32]1

Participants

8

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 68289SesamolHCID 54166583HCID 54166583, compound

Product 1

HCID 54373732HCID 54373732, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (308 mg, 7.69 mmol) was added to a solution of sesamol (967 mg, 6.99 mmol) in dry THF (5 ml), and the solution was stirred at room temperature for 20 minutes. The THF was then removed under pressure and the remaining sodium salt of sesamol was placed under vacuum for 10 minutes. Dry DMSO (8 ml) followed immediately by ethyl-2-fluoro-6-[2-(1-propenyl)-3,4 (methylenedioxy)phenoxy]benzoate (2.41 g, 6.99 mmol) in dry DMSO were added. The resulting dark brown mixture was heated at 80° C. for 18 h. Water (30 ml) followed by ethyl acetate (50 ml) was added to the reaction mixture upon cooling and the layers were separated. The aqueous layer was extracted with an additional 50 ml of EtOAC. The combined organic fractions was then washed with brine and dried over MgSO4. Evaporation of solvents yielded an oil which was purified by flash column chromatography using 5-10%-ethyl acetate-hexanes giving 1.4 g (43%) of the unsaturated ester as a yellow oil.

Workup

  1. customThe THF was then removed under pressure
  2. waitthe remaining sodium salt of sesamol was placed under vacuum for 10 minutes
  3. additionwere added
  4. temperatureThe resulting dark brown mixture was heated at 80° C. for 18 h
  5. additionwas added to the reaction mixture
  6. temperatureupon cooling
  7. customthe layers were separated
  8. extractionThe aqueous layer was extracted with an additional 50 ml of EtOAC
  9. washThe combined organic fractions was then washed with brine
  10. dry with materialdried over MgSO4
  11. customEvaporation of solvents
  12. customyielded an oil which
  13. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-ccda16b94c57480e80540487bf9015cb
Source dataset
uspto-grants-1999_11
Patent number
US05977117

Reaction notes

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