Triethylamine → Ethyl 5-methyl-1,3,4-oxadiazole-2-carboxylate

HRID 2246379Notes

Reaction equation

HRID 2246379 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH3:2].C(N(CC)CC)C>C(Cl)Cl>[CH3:2][C:1]1[O:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 13407459Ethyl 2-(2-acetylhydrazinyl)-2-oxoacetate

Product 1

HCID 13407467Ethyl 5-methyl-1,3,4-oxadiazole-2-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-(2-acetylhydrazinyl)-2-oxoacetate (0.50 g, 2.87 mmol) in CH2Cl2 (10 mL) was added triethylamine (0.53 mL, 3.73 mmol) and p-TsCl (0.65 g, 3.44 mmol) in three portions. The reaction mixture was stirred at rt for 8 h then was diluted with CH2Cl2 and washed with water. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude was purified by column chromatography using EtOAc/hexanes to give the title compound as an off-white solid (375 mg, 84%). 1H NMR (300 MHz, CDCl3): δ 4.51 (2H, q, J=7 Hz), 2.65 (3H, s), 1.52 (3H, t, J=5 Hz). MS (M+H): 157.1.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-c1e74a36cb104aecae5dcb9ba0c45391
Source dataset
uspto-grants-2010_03
Patent number
US07687509B2

Reaction notes

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