Toluene → ethyl (2E)-2-(benzylhydrazinylidene)acetate

HRID 571611Notes

Reaction equation

HRID 571611 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=O.C1(C)C=CC=CC=1.Cl.[CH2:16]([NH:23][NH2:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH2:16]([NH:23]/[N:24]=[CH:2]/[C:1]([O:5][CH2:6][CH3:7])=[O:4])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 14084Hydrazine, (phenylmethyl)-, hydrochloride (1:1)HCID 70211Ethyl oxoacetate

Product 1

HCID 14932645ethyl (2E)-2-(benzylhydrazinylidene)acetateYield 53%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

47% ethyl glyoxylate in toluene (polymer type) (29.2 g, 134.5 mmol) was dissolved in THF (200 ml), and to the solution was added benzylhydrazine monohydrochloride (21.3 g, 134.5 mmol) and triethylamine (20.6 ml, 148 mmol), and stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 14.9 g of E-ethyl 2-(2-benzylhydrazono)acetate (mixture of E:Z=4:1) (yield: 53%) as oil.

Workup

  1. washwashed with water
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c8e08f4f6dba440a8530cc9c6e4234fb
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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