Water → 3-(5-Methyl-1,2-oxazol-3-yl)propan-1-ol
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux for three hours
- temperaturecooled
- filtrationThe mixture was filtered
- concentrationthe filtrate concentrated in vacuo
- 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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