Ammonium Chloride → CID 275522

HRID 873441Notes

Reaction equation

HRID 873441 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-9edfb86f95104072ad3405ded206c86c
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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