Triethylamine → 3-Ethyl 3,5-isoxazoledicarboxylate

HRID 1409380ノート

反応式

HRID 1409380 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 216484863-Ethyl 3,5-isoxazoledicarboxylate収率 60.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7f4917728dca4395b042b45f42a5519d
出典データセット
uspto-grants-2014_12
特許番号
US08921378B2

反応ノート

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