Ethyl pyruvate → HCID 13675760, compound

HRID 880905Notes

Reaction equation

HRID 880905 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=O.Cl.[C:10]([NH:14][NH2:15])([CH3:13])([CH3:12])[CH3:11].C(N(CC)C(C)C)(C)C>C(O)C>[C:10]([NH:14]/[N:15]=[C:2](\[CH3:4])/[C:1]([O:6][CH2:7][CH3:8])=[O:5])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 12041Ethyl pyruvateHCID 81531DiisopropylethylamineHCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 13675760HCID 13675760, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl pyruvate (20.22 g, 174.1 mmol) in ethanol (150 mL) was added t-butyl hydrazine hydrochloride (21.7 g, 174 mmol) and N,N-diisopropylethyl amine (33.4 mL, 192 mmol). After stirring at reflux for 18 hours, the reaction was cooled and the volatiles were removed under reduced pressure. The resultant golden oil was taken up in 300 mL ethyl acetate and washed with 200 mL water and 300 mL saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and concentrated to yield (E)-ethyl 2-(2-tert-butylhydrazono)propanoate (23.1 g) as a clear pale yellow oil. +APCI (M+H) 187.3; 1H NMR (400 MHz, CDCl3, δ): 5.51 (br. s., 1H), 4.25 (q, J=7.2 Hz, 2H), 1.89 (s, 3H), 1.32 (t, J=7.1 Hz, 3H), 1.28 (s, 9H).

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturethe reaction was cooled
  3. customthe volatiles were removed under reduced pressure
  4. washwashed with 200 mL water and 300 mL saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e96d901d49e0422cb7b8ae5ee94ad5fd
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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