Ammonium Chloride → CID 275522

HRID 42490

Reaction equation

HRID 42490 reaction equation
[O:1]=[C:2]([CH2:8][C:9](=[O:11])[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(OCC)(OCC)O[CH2:14][CH3:15].[Cl-].[NH4+]>C(O)C>[CH2:14]([O:11][C:9]([CH3:10])=[CH:8][C:2](=[O:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:15]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 31214Ethyl orthoformateHCID 69208Ethyl 2,4-dioxovalerate

Product 1

HCID 275522CID 275522Yield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 2,4-dioxopentanoate (36.5 g, 231 mmol) and triethyl orthoformate (41 mL, 246 mmol) in ethanol (60 mL) was added ammonium chloride (3.7 g, 69 mmol). The suspension was stirred at RT overnight. LCMS showed that the reaction was mostly complete. (Hydrolyzes on LCMS to some degree?) The reaction was concentrated under vacuum. The remaining oil was taken up in Et2O (300 mL), filtered to remove insolubles, rinsed with Et2O, and concentrated under vacuum. The product was obtained by short path distillation under vacuum (bp 70 to 77° C. at 0.09 mmHg) to give the product ethyl 4-ethoxy-2-oxopent-3-enoate (36.5 g, 47.3 mmol, 79% yield) as a light yellow oil.

Workup

  1. concentration) The reaction was concentrated under vacuum
  2. filtrationfiltered
  3. customto remove insolubles
  4. washrinsed with Et2O
  5. concentrationconcentrated under vacuum
  6. customThe product was obtained by short path distillation under vacuum (bp 70 to 77° C. at 0.09 mmHg)

Sources & evidence

ORD record
ord-b160e798a785465a9a8987f6922ce044
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Linked notes

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