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

HRID 1905505Notes

Reaction equation

HRID 1905505 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-afaf8fee96484132bb39c7a0a2ac6526
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

Loading…