Triethylamine → 3-(4-Nitro-phenyl)-isoxazole-5-carboxylic acid ethyl ester

HRID 75759

反応式

HRID 75759 の反応式
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[C:15]#[CH:16].CCN(CC)CC>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:19]([O:18][C:14]([C:15]1[O:1][N:2]=[C:3]([C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=2)[CH:16]=1)=[O:17])[CH3:20]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 12182Ethyl propiolateHCID 915274alpha-Chloro-4-nitrobenzaldoxime

生成物 1

HCID 9493753-(4-Nitro-phenyl)-isoxazole-5-carboxylic acid ethyl ester収率 51.7%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of N-hydroxy-4-nitro-benzimidoyl chloride (2.0 g; 10 mmol) and ethyl propiolate (2.02 ml; 20 mmol) in toluene (25 ml) was added Et3N (1.46 ml; 10.5 mmol) drop wise for 10 minutes. The resulting reaction mixture was heated at 80° C. for 2.5 hours, and then diluted with EtOAc (50 ml) and transferred in a separating funnel. The EtOAc layer was washed with 0.1N HCl (10 ml) followed by water (3×10 ml) and brine (10 ml). The EtOAc layer was dried over anhydrous Na2SO4, solvent was evaporated and the residue was crystallized from CHCl3 and light petroleum to afford the title compound of step 1 (1.35 g; 51.7%). Mass (ES+), 263 (M++1); 1H NMR (CDCl3) δ: 1.45 (t, 3H), 4.48 (q, 2H), 7.26 (s, 1H), 8.02 (d, 2H), 8.35 (d, 2H).

後処理

  1. customThe resulting reaction mixture
  2. customtransferred in a separating funnel
  3. washThe EtOAc layer was washed with 0.1N HCl (10 ml)
  4. dry with materialThe EtOAc layer was dried over anhydrous Na2SO4, solvent
  5. customwas evaporated
  6. customthe residue was crystallized from CHCl3 and light petroleum

出典と根拠

ORDレコード
ord-4057b49b7fde4dd7b211e637d8014c1a
出典データセット
uspto-grants-2014_09
特許番号
US08835428B2

関連ノート

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