Sulfuric Acid → 3-Ethyl 3,5-isoxazoledicarboxylate

HRID 58530

반응식

HRID 58530 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

HCID 216484863-Ethyl 3,5-isoxazoledicarboxylate수율 70%

시약·촉매·용매 4

HCID 10219390chromium (VI) trioxide촉매HCID 180Acetone용매HCID 962Water용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c56278181277486b80a005166deef8df
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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