Ethanol → HCID 18325846, compound

HRID 1251023Notes

Reaction equation

HRID 1251023 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH:15]([C:17]([CH3:19])=[O:18])=[CH2:16].[CH3:20]CO>CC[O-].[Na+]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:9]([CH2:16][CH2:15][C:17](=[O:18])[CH3:19])[C:10]([O:12][CH2:13][CH3:20])=[O:11])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6570Methyl vinyl ketoneHCID 291780methyl 3-(4-methylphenyl)-3-oxopropanoate

Product 1

HCID 18325846HCID 18325846, compound

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideCatalyst

Procedure

To a stirred solution of methyl 3-(4-methylphenyl)-3-oxopropanoate(2.28 g, 11.1 mmol) in EtOH(10 ml), NaOEt(11 mg, 0.16 mmol) was added and methyl vinyl ketone(2.0 g, 27.8 mmol) was added dropwise less than 25° C. After stirring the reaction mixture for 30 min. less than 25° C., the solvent was evaporated under reduced pressure. Dil.HCl aq. was added to the residue and extracted by EtOAc. The organic layer was washed with water and brine, dried over MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel with n-hexane-AcOEt to afford 2.73 g of ethyl 2-((4-methylphenyl)carbonyl)-5-oxohexanoate as a pale yellow oil (y=89.0%). 1H-NMR(ppm, 300 MHz, CDCl3) δ 7.92(2H, d, J=8.0 Hz), 7.28(2H, d, J=8.0 Hz), 4.41(1H, t, J=7.0 Hz), 4.14(2H, q, J=6.9 Hz), 2.55-2.60(2H, m), 2.13(3H, s), 1.17(3H, t, J=6.9 Hz).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionHCl aq. was added to the residue
  3. extractionextracted by EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customAfter removal of the solvent
  7. customthe residue was purified by column chromatography on silica gel with n-hexane-AcOEt

Sources & evidence

ORD record
ord-a6a77fae6c4140e8b0ba6bd4036633cc
Source dataset
uspto-grants-2002_01
Patent number
US06340772B1

Reaction notes

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