Sulfuric Acid → 3-Ethyl 3,5-isoxazoledicarboxylate

HRID 58530

反応式

HRID 58530 の反応式
OS(O)(=O)=O.[OH:6][CH2:7][C:8]1[O:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=1.CC([OH:21])C.C(OCC)(=O)C>O.CC(C)=O.[Cl-].[Na+].O.[O-2].[Cr+6].[O-2].[O-2]>[CH2:16]([O:15][C:13]([C:10]1[CH:9]=[C:8]([C:7]([OH:21])=[O:6])[O:12][N:11]=1)=[O:14])[CH3:17]

参加物

9

反応物 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 8027233Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

生成物 1

HCID 216484863-Ethyl 3,5-isoxazoledicarboxylate収率 70%

試薬・触媒・溶媒 4

HCID 10219390chromium (VI) trioxide触媒HCID 180Acetone溶媒HCID 962Water溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A 2M solution of the Jone's reagent was prepared by addition of 6 g of chromium (VI) oxide to a solution of H2SO4 (8.1 g) in water (25.5 mL). To a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (4.00 g; 23.37 mmol) in acetone in an ice bath was added dropwise during a period of 20 min the Jone's reagent (27.71 mL; 51.42 mmol). The reaction mixture was then stirred at room temperature for additional 3.5 hours. 5 mL of 2-propanol were added and the stirring continued for further 1 hour. The solution became green. Brine (60 mL) and ethyl acetate (150 mL) were added to the reaction mixture and after separation, the organic layer was washed with an aqueous solution of sodium bisulphite (15 g in 100 mL of H2O) and with brine (100 mL). The organic layer was dried over magnesium sulfate. The evaporation of the solution furnished 3.03 g (70%) of 3-(ethoxycarbonyl)isoxazole-5-carboxylic acid as a white solid.

後処理

  1. waitthe stirring continued for further 1 hour
  2. customafter separation
  3. washthe organic layer was washed with an aqueous solution of sodium bisulphite (15 g in 100 mL of H2O) and with brine (100 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customThe evaporation of the solution

出典と根拠

ORDレコード
ord-c56278181277486b80a005166deef8df
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

関連ノート

読み込み中…