Ethyl 3-(3-methoxy-2-methylphenyl)-3-oxopropanoate → Ethyl 3-(3-methoxy-2-methylphenyl)propanoate

HRID 1821032Notes

Reaction equation

HRID 1821032 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]([C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 68850344Ethyl 3-(3-methoxy-2-methylphenyl)-3-oxopropanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 68850412Ethyl 3-(3-methoxy-2-methylphenyl)propanoateYield 83.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution ethyl 3-(3-methoxy-2-methylphenyl)-3-oxopropanoate (137.2 g, 595 mmol, from Step A) in ethyl alcohol (924 mL), 10% Pd—C (13.7 g) was added and 3 atm of hydrogen were applied. The mixture was heated to 60° C. for 20 hr, cooled to ambient temperature and filtered through Celite®. The filtrate was concentrated in vacuo and the residue purified by flash chromatography (2% EtOAc/hexanes) on SiO2 to afford 110.8 g of the title compound as a pale yellow liquid: 1H NMR (500 MHZ, CDCl3) δ 1.25 (t, 3H, J=7.1 Hz), 2.19 (s, 3H), 2.55 (t, 2H, J=8.0 Hz), 2.95 (t, 2H, J=8.0 Hz), 3.82 (s, 3H), 4.14 (q, 2H, J=7.1 Hz), 6.73 (d, 1H, J=8.2 Hz), 6.78 (d, 1H, J=7.6 Hz), 7.10 (d, 1H, J=7.9 Hz).

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered through Celite®
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by flash chromatography (2% EtOAc/hexanes) on SiO2

Sources & evidence

ORD record
ord-bbedefefb6dc4ccea9266473bf9f9071
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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