Ethyl Acetate → HCID 54452584, compound

HRID 377307

Reaction equation

HRID 377307 reaction equation
C(C(CC)(P(O)(O)=O)C(O)=O)C.[H-].[Na+].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]2[CH2:27][CH2:26][CH2:25][C:24]2=O)[CH:20]=[CH:21][CH:22]=1.[C:29]([O:32][CH2:33][CH3:34])(=[O:31])[CH3:30]>COCCOC.O>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[O:31])[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 123629382-(3-Methoxyphenyl)cyclopentan-1-oneHCID 17786294Diethyl phosphonoacetic acid

Product 1

HCID 54452584HCID 54452584, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of diethyl phosphono acetic acid (8.0 ml) in 1,2-dimethoxyethane (80 ml) was added sodium hydride (60% in oil, 1.4 g) at 0° C. under N2. After being stirred for 1 hour at ambient temperature, to the solution was added a solution of 2-(3-methoxyphenyl)cyclopentanone (4.5 g) in 1,2-dimethoxyethane (20 ml). After being stirred for 12 hours, the reaction mixture was poured into a mixture of ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate aqueous solution and brine. The dried solvent was concentrated and the obtained residue was purified by column chromatography on silica gel to give ethyl [2-(3-methoxyphenyl)cyclopentylidene]acetate (5.0 g).

Workup

  1. stirringAfter being stirred for 12 hours
  2. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  3. concentrationThe dried solvent was concentrated
  4. customthe obtained residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ad95da0c036d498085df69c8c0bc077e
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Linked notes

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