Formaldehyde → Ethyl 4-formylpent-4-enoate

HRID 654655

Reaction equation

HRID 654655 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl-].[CH3:12][NH2+]C.C=O>>[CH:2]([C:3](=[CH2:12])[CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:1]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 11137279Ethyl 5-oxopentanoateHCID 12954980Dimethylazanium;chloride

Product 1

HCID 13223493Ethyl 4-formylpent-4-enoate

Procedure

With stirring, 14.4 g (100 mmol) of ethyl 5-oxopentanoate, 9.2 g (112.6 mmol) of dimethylammonium chloride and 10.8 ml (117 mmol) of 37% formaldehyde solution are heated to 100° C. The mixture is cooled and extracted with 3×30 ml of diethyl ether. The batch is cooled and the organic phases are combined, washed with a saturated solution of sodium chloride, dried over magnesium sulfate and evaporated to dryness, giving ethyl 4-formylpent-4-enoate as a colorless oil which can be further reacted without additional purification.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with 3×30 ml of diethyl ether
  3. temperatureThe batch is cooled
  4. washwashed with a saturated solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-59533b96b685417084f5f39be02b0e1e
Source dataset
uspto-grants-1992_07
Patent number
US05134134

Linked notes

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