Water → 1,4-Diethyl 2-formylbutanedioate

HRID 2353320Notes

Reaction equation

HRID 2353320 reaction equation
[Na].[C:2]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:14](OCC)=[O:15].O>C(OCC)C>[CH:14]([CH:3]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:2]([O:11][CH2:12][CH3:13])=[O:10])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 31249Diethyl SuccinateHCID 5360545Sodium2×

Product 1

HCID 2315001,4-Diethyl 2-formylbutanedioateYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of sodium (1.66 g, 72.13 mmol) in diethyl ether (35 mL) was added diethyl succinate (10 mL, 60.11 mmol) and ethyl formate (8.25 mL, 102.18 mmol) at room temperature, and the reaction mixture was refluxed for 5 hours. After the cooling to room temperature, water was added to the mixture until the sodium salt was dissolved completely and aqueous layer was separated. The aqueous layer was neutralized by 6M hydrochloric acid (10.8 mL) and extracted with diethyl ether. The extracts were washed with sat.NaHCO3, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by distillation (115-120° C., 10 mmHg) to give diethyl 2-formylsuccinate (6.55 g, 54%) as colorless oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 hours
  2. dissolutionwas dissolved completely
  3. customaqueous layer was separated
  4. extractionextracted with diethyl ether
  5. washThe extracts were washed
  6. dry with materialNaHCO3, dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. distillationThe crude product was purified by distillation (115-120° C., 10 mmHg)

Sources & evidence

ORD record
ord-821735a0156a4ce69696f56bb9733a4b
Source dataset
uspto-grants-2010_07
Patent number
US07750014B2

Reaction notes

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