Water → 3-(5-Methyl-1,2-oxazol-3-yl)propan-1-ol

HRID 1905482Notes

Reaction equation

HRID 1905482 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][N:11]=[C:10]([CH2:13][CH2:14][C:15](OC)=[O:16])[CH:9]=1.O>O1CCCC1>[CH3:7][C:8]1[O:12][N:11]=[C:10]([CH2:13][CH2:14][CH2:15][OH:16])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 573461Methyl 5-methyl-3-isoxazolepropanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 133169743-(5-Methyl-1,2-oxazol-3-yl)propan-1-olYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 7.6 g of lithium aluminum hydride in 250 ml of tetrahydrofuran was added a solution of 64.9 g of methyl 5-methyl-3-isoxazolepropanoate in 100 ml of tetrahydrofuran. The reaction mixture was stirred at reflux for three hours, then cooled and 15.2 ml of water in 30 ml of tetrahydrofuran added. The mixture was filtered and the filtrate concentrated in vacuo. The residue was distilled to give 44.1 g of 5-methyl-3-(3-hydroxypropyl)isoxazole, b.p. 84°-85° C.(0.1 mm).

Workup

  1. temperatureat reflux for three hours
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. distillationThe residue was distilled

Sources & evidence

ORD record
ord-927793b70292498dba474c9f67c0530c
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

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