Ethyl Acetate → HCID 23090910, compound

HRID 1819996Notes

Reaction equation

HRID 1819996 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)(=O)[CH3:2].C(OP(CC(OCC)=O)(OCC)=O)C.C(O[K])(C)(C)C.[C:35]([O:38][CH2:39][CH3:40])(=[O:37])[CH3:36]>O1CCCC1>[CH2:39]([O:38][C:35](=[O:37])[CH2:36][CH:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)[CH3:2])[CH3:40]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13345Triethyl phosphonoacetateHCID 600911Ethyl 4-acetylbenzoateHCID 178418922HCID 178418922, compound

Product 1

HCID 23090910HCID 23090910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-acetylbenzate (5.00 g, 26.0 mmol) was added to a solution (130 ml) of ethyl diethylphosphonoacetate (6.71 ml, 33.8 mmol) and tert-butoxy potassium (4.38 g, 39.0 mmol) in tetrahydrofuran at 0° C., and the mixture was stirred at room temperature for 16 hrs. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate). The mixture of the obtained oil and 10% palladium carbon (1 g) in ethanol (150 ml) was stirred under a hydrogen atmosphere for 2 hrs, and filtered through celite. The solvent was evaporated under reduced pressure, and the obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate) to give the title compound (5.67 g).

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate)
  5. additionThe mixture of the obtained oil and 10% palladium carbon (1 g) in ethanol (150 ml)
  6. stirringwas stirred under a hydrogen atmosphere for 2 hrs
  7. filtrationfiltered through celite
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record
ord-0a9e1d7fdc7d4cadb8085402ff590ad3
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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