Ethanol → Ethyl 5-cyclobutyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate

HRID 646006

反応式

HRID 646006 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[CH:4]=[N:5][OH:6].ClN1C(=O)CCC1=O.[CH:20]1([C:24](=O)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:23][CH2:22][CH2:21]1.[O-]CC.[Na+].C(O)C>CN(C=O)C.O1CCCC1.O>[CH:20]1([C:24]2[O:6][N:5]=[C:4]([C:3]3[C:2]([Cl:1])=[CH:10][CH:9]=[CH:8][C:7]=3[Cl:11])[C:25]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:21][CH2:22][CH2:23]1

参加物

9

反応物 5

HCID 702EthanolHCID 31398ChlorosuccinimideHCID 91328Benzaldehyde, 2,6-dichloro-, oximeHCID 2723922Sodium ethoxideHCID 21846412Ethyl 3-cyclobutyl-3-oxopropanoate

生成物 1

HCID 59264874Ethyl 5-cyclobutyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate収率 38%

試薬・触媒・溶媒 3

HCID 962Water溶媒3 回HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2,6-dichlorobenzaldehyde oxime (2.2 g, 11.6 mmol) in N,N,-dimethylformamide (7 mL) cooled in a water bath was added solid N-chlorosuccinimide (1.5 g, 11.6 mmol). The solution was stirred with the flask in the water bath for approximately 20 minutes and then with the flask out of the bath for approximately 1 hour. The solution was poured into water and then extracted twice with ether. The combined organic phases were dried over magnesium sulfate and concentrated. To a separate solution of ethyl 3-cyclobutyl-3-oxopropanoate (2.4 g, 13.9 mmol) in tetrahydrofuran (3 mL) at 0° C. was added a 3.16 M solution of sodium ethoxide in ethanol (4.4 mL, 13.9 mmol) quickly. The solution was stirred for a few minutes. To that solution was added the isolated imidoyl chloride in tetrahydrofuran (5 mL) dropwise. The solution was stirred at 0° C. for approximately 1 h and then allowed to stir at ambient temperature overnight. The solution was poured into water and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated and purified by chromatography (silica gel, 0-5% ethyl acetate in hexanes gradient elution) to afford a white solid (1.5 g, 38%). 1H-NMR (DMSO-d6) δ 7.63-7.53 (m, 3H), 4.25 (quintet, J=9 Hz, 1H), 4.02 (q, J=7 Hz, 2H), 2.43-2.36 (m, 4H), 2.15-1.89 (m, 2H), 0.94 (t, J=7 Hz, 3H).

後処理

  1. extractionextracted twice with ether
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated
  4. stirringThe solution was stirred at 0° C. for approximately 1 h
  5. stirringto stir at ambient temperature overnight
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by chromatography (silica gel, 0-5% ethyl acetate in hexanes gradient elution)

出典と根拠

ORDレコード
ord-b56950cc4b0946b6af12eb34fae074df
出典データセット
uspto-grants-2010_04
特許番号
US07705028B2

関連ノート

読み込み中…