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

HRID 2165383Notes

Reaction equation

HRID 2165383 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 aluminium 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-7cb2ae5e56aa416ab693e4f1cdad4d60
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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