Triethylamine → Ethyl 4-methyl-3-(pyridin-4-yl)isoxazole-5-carboxylate

HRID 2388195ノート

反応式

HRID 2388195 の反応式
O[N:2]=[C:3]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH:4]([CH3:12])[C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(CC)CC)C.S(Cl)(C)(=O)=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:12][C:4]1[C:3]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:2][O:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136341743Ethyl 4-(hydroxyimino)-3-methyl-2-oxo-4-(pyridin-4-yl)butanoate

生成物 1

HCID 67530753Ethyl 4-methyl-3-(pyridin-4-yl)isoxazole-5-carboxylate収率 117.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

Ethyl 4-(hydroxyimino)-3-methyl-2-oxo-4-(pyridin-4-yl)butanoate (4.68 g, 18.7 mmol) and triethylamine (3.4 mL, 24.3 mmol) were added to 120 mL of CH2Cl2. Mesyl chloride (1.9 mL, 24.3 mmol) was added and the mixture was stirred at room temperature for 20 h. The reaction mixture was diluted with CH2Cl2 and saturated sodium bicarbonate solution was added. The aqueous layer was extracted with additional CH2Cl2 and the combined organic layer was washed with brine and dried over MgSO4. The solvent was removed in vacuo to afford 5.1 g of the title compound. MS: (+) m/z 233.35 (M+1).

後処理

  1. additionwas added
  2. extractionThe aqueous layer was extracted with additional CH2Cl2
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-7c056bbdc96d40ccb101012d47146253
出典データセット
uspto-grants-2012_09
特許番号
US08269008B2

反応ノート

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