Ethyl formate → Ethyl 2-(benzyloxy)-3-oxopropanoate

HRID 1774432Notes

Reaction equation

HRID 1774432 reaction equation
[H-].[Na+].[CH:3]([O:5][CH2:6][CH3:7])=[O:4].C([O:10][C:11](=O)[CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C>CCOCC>[CH2:14]([O:13][CH:12]([CH:11]=[O:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 290299Ethyl 2-(benzyloxy)acetate

Product 1

HCID 19903223Ethyl 2-(benzyloxy)-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of sodium hydride (3.3 g, 60% in paraffin oil, 82.5 mmol) in dry ether (100 mL) and dry ethyl formate (5.55 g, 75 mmol) was added ethyl(benzyloxy)acetate (14.57 g, 75 mmol) dropwise with stirring. The resulting mixture solution was then refluxed for 2 h and concentrated to give crude ethyl 2-(benzyloxy)-3-oxopropanoate which was used in the subsequent step without further purification.

Workup

  1. temperatureThe resulting mixture solution was then refluxed for 2 h
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-20ac485fa36648d1ac8954084203c358
Source dataset
uspto-grants-2016_02
Patent number
US09260413B2

Reaction notes

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