Triethylamine → 3-Ethyl 3,5-isoxazoledicarboxylate

HRID 1409380Notes

Reaction equation

HRID 1409380 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[C:10]([OH:14])(=[O:13])[C:11]#[CH:12].C(N(CC)CC)C>C(OCC)C>[CH2:2]([O:3][C:4]([C:6]1[CH:12]=[C:11]([C:10]([OH:14])=[O:13])[O:8][N:7]=1)=[O:5])[CH3:1]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 10110Propiolic AcidHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

Product 1

HCID 216484863-Ethyl 3,5-isoxazoledicarboxylateYield 60.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Ethyl chlorooximidoacetate (3.30 mmol, 0.5 g) and propiolic acid (33.0 mmol, 2.311 g) were dissolved in diethyl ether (10 ml) with stirring. Triethylamine (3.30 mmol, 0.334 g) dissolved in diethyl ether (5 ml) was added dropwise to the previous mixture. The reaction mixture was stirred for three days at RT during which more triethylamine (2×0.668 g dissolved in 5 ml diethyl ether) was added dropwise. The pH of the reaction mixture was adjusted to 2. The organic phase was washed twice with water. The organic phase was dried, filtered and evaporated. The residue was dried under vacuum. 369 mg of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 1.44 (t, 3H), 4.49 (q, 2H), 7.41 (s, 1H), 10.59 (bs, 1H).

Workup

  1. additionwas added dropwise to the previous mixture
  2. additionwas added dropwise
  3. washThe organic phase was washed twice with water
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-7f4917728dca4395b042b45f42a5519d
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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