Triethylamine → 3-Ethyl 3,5-isoxazoledicarboxylate

HRID 1409380

반응식

HRID 1409380 반응식
[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]

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 10110Propiolic AcidHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

생성물 1

HCID 216484863-Ethyl 3,5-isoxazoledicarboxylate수율 60.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7f4917728dca4395b042b45f42a5519d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921378B2

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