Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11](=[O:13])[N:10]([CH2:14][CH2:15][O:16][CH3:17])[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(O[CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][O:32][CH2:31]1)(=O)(=O)C>C(#N)C>[O:32]1[CH2:33][CH2:34][CH2:35][CH:30]([CH2:29][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[O:12][C:11](=[O:13])[N:10]([CH2:14][CH2:15][O:16][CH3:17])[N:9]=3)=[CH:6][CH:7]=2)[CH2:31]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2 g of 5-(4-hydroxyphenyl)-3-methoxyethyl-1,3,4-oxadiazol-2(3H)-one are dissolved in acetonitrile, followed by addition of 2.92 g of potassium carbonate and a solution of 3.12 g of 3-tetrahydropyranylmethyl mesylate in acetonitrile. The mixture is heated to reflux for 5 h and then filtered, diluted with ethyl acetate and washed with three times 50 ml of 2N sodium hydroxide. The organic phase is then washed with water until neutral, dried over sodium sulphate and filtered, and the solvent is then evaporated off. After two recrystallizations in diisopropyl ether, 0.7 g of product is obtained.
Workup
- temperatureThe mixture is heated
- temperatureto reflux for 5 h
- filtrationfiltered
- additiondiluted with ethyl acetate
- washwashed with three times 50 ml of 2N sodium hydroxide
- washThe organic phase is then washed with water until neutral,
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customthe solvent is then evaporated off
- customAfter two recrystallizations in diisopropyl ether
Sources & evidence
- ORD record
- ord-9b29115ceef74d24b337e790c9a81ac4
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05525619
Linked notes
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