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

HRID 1287685Notes

Reaction equation

HRID 1287685 reaction equation
[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

Participants

5

Reactant 3

HCID 24436Sodium Sulfate2×HCID 736348Ethyl 3,5-dimethylisoxazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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-carbo-ethoxy-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°.

Workup

  1. additionA suspension of 100 g
  2. temperatureto maintain a gentle reflux
  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

Sources & evidence

ORD record
ord-afb4d1c5f7a04e0eb07f08cfba39adf3
Source dataset
uspto-grants-1976_10
Patent number
US03985771

Reaction notes

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