Sodium Sulfate → 3,5-Dimethyl-4-(hydroxymethyl)isoxazole

HRID 1287362

반응식

HRID 1287362 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:12]1[C:13]([CH3:18])=[N:14][O:15][C:16]=1[CH3:17])(OCC)=[O:8].S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH3:18][C:13]1[C:12]([CH2:7][OH:8])=[C:16]([CH3:17])[O:15][N:14]=1

참가 물질

5

반응물 3

HCID 24436Sodium Sulfate2회HCID 736348Ethyl 3,5-dimethylisoxazole-4-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 2895753,5-Dimethyl-4-(hydroxymethyl)isoxazole

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A suspension of 100 g (2.63 moles) of lithium aluminum hydride in 2.5 liters of anhydrous ether was stirred under nitrogen as a solution of 272 g. (1.61 mole) of the 4-carboethoxy-3,5-dimethylisoxazole prepared in Example 1 above in 400 ml. of anhydrous ether was added at such a rate as to maintain a gentle reflux. The suspension was stirred at room temperature under nitrogen overnight, during which time an extremely gummy green-gray mass formed in the bottom of the flask. The mixture was cooled in an ice bath and hydrolyzed with saturated aqueous sodium sulfate solution. Anhydrous sodium sulfate was added to dry the ether solution. The salts were removed by filtration and washed carefully with ether and chloroform. Solvent removal from the filtrates, finally at 50°/0.1 mm., gave a white crystalline mass. This was triturated with hot ether and then cooled. Filtration gave 3,5-dimethyl-4-hydroxymethyl-isoxazole as white prisms, m.p. 76.5°/77.5°. Concentration of the mother liquors gave a second crop of prisms, m.p. 76.5°-78°.

후처리

  1. temperatureto maintain a gentle reflux
  2. stirringThe suspension was stirred at room temperature under nitrogen overnight, during which time an extremely gummy green-gray mass
  3. customformed in the bottom of the flask
  4. dry with materialto dry the ether solution
  5. customThe salts were removed by filtration
  6. washwashed carefully with ether and chloroform
  7. customSolvent removal from the filtrates
  8. customfinally at 50°
  9. custom, gave a white crystalline mass
  10. customThis was triturated with hot ether
  11. temperaturecooled
  12. filtrationFiltration

출처 및 근거

ORD 기록
ord-ed38425886134226acc4429ca55b6429
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03984428

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