Water → Ethyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoate

HRID 460726Notes

Reaction equation

HRID 460726 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C1(C)C=CC=CC=1>[CH2:8]([O:7][C:3](=[O:10])[CH2:26][C:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:20][CH:21]=1)=[O:27])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Product 1

HCID 4316945Ethyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoateYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a refluxing mixture of 7.0 g (175 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) and 10.45 g (88.5 mmol) of diethyl carbonate (CO(OEt)2) in 100 mL of toluene was added dropwise via an addition funnel a mixture of 10 g (44.3 mmol) of 1-(4-benzyloxy-phenyl)-ethanone in 20 mL of toluene, and the resulting mixture was heated at reflux under argon for 1 h. The reaction mixture was then cooled to 0° C., quenched by the addition of 40 mL of acetic acid, during which time a yellow precipitate formed, and it dissolved upon subsequent addition of water. The separated organic layer was washed with saturated sodium bicarbonate solution, water and brine, dried over sodium sulfate and concentrated to give a residue which was chromatographed on silica gel (10% hexane in dichloromethane) to afford 9.2 g (70% yield) of desired 3-(4-benzyloxy-phenyl)-3-oxo-propionic acid ethyl ester as indicated by 1H NMR.

Workup

  1. additionwas added dropwise via an addition funnel
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux under argon for 1 h
  4. customquenched by the addition of 40 mL of acetic acid, during which time a yellow precipitate
  5. customformed
  6. washThe separated organic layer was washed with saturated sodium bicarbonate solution, water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a residue which
  10. customwas chromatographed on silica gel (10% hexane in dichloromethane)

Sources & evidence

ORD record
ord-af58fa18ea29476e9027877cef19c632
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Reaction notes

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