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

HRID 869301Notes

Reaction equation

HRID 869301 reaction equation
[H-].[Na+].[CH:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:8]([O:15][CH2:16][C:17](OCC)=[O:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOCC>[CH2:8]([O:15][CH:16]([CH:17]=[O:18])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=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-bf3ba2740770454b819b381849387ac0
Source dataset
uspto-grants-2015_03
Patent number
US08969364B2

Reaction notes

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