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

HRID 359822

Reaction equation

HRID 359822 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 SulfateHCID 736348Ethyl 3,5-dimethylisoxazole-4-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 2895753,5-Dimethyl-4-(hydroxymethyl)isoxazoleYield 75.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 23.53 g of lithium aluminum hydride in 600 ml of ether was added dropwise 64 g of 4-carbethoxy-3,5-dimethylisoxazole in 100 ml of ether at a rate so that gentle reflux occurred. The addition was complete in about two hours, and the mixture was stirred overnight under nitrogen. A saturated solution of sodium sulfate was added dropwise under nitrogen until the excess lithium aluminum hydride was decomposed. The resulting suspension was filtered and the filtrate concentrated to an oil which was distilled to give 36.4 g of 3,5-dimethyl-4-hydroxymethylisoxazole, b.p. 130°-140° C. (0.1 mm).

Workup

  1. temperaturethat gentle reflux
  2. additionThe addition
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate concentrated to an oil which
  5. distillationwas distilled

Sources & evidence

ORD record
ord-216dd9ccd641402aab34f64cd3767c27
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Linked notes

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