Triethylamine → Methyl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11](Cl)=[N:12][OH:13])=[CH:7][CH:6]=1)=[O:4].[CH2:15]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>O1CCCC1.ClCCl>[CH2:15]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:13][N:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[CH:28]=2)=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH2:18][CH3:19]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 4-Methoxycarbonylphenylhydroxyiminomethyl chloride (16.98 g) and 4-n-pentyloxyphenylacetylene (18.96 g) in tetrahydrofuran (170 ml) was added triethylamine (14.4 ml) in tetrahydrofuran (140 ml) over a period of 2 hours at 40° C. and the mixture was stirred at 40° C. for 30 minutes. The mixture was diluted with dichloromethane and washed with water and brine. The separated organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with acetonitrile. The precipitate was collected by filtration and dried to give Methyl 4-[5-(4-n-pentyloxyphenyl)isoxazol-3-yl]benzoate (24.56 g).
Workup
- washwashed with water and brine
- dry with materialThe separated organic layer was dried over magnesium sulfate
- customevaporated under reduced pressure
- customThe residue was triturated with acetonitrile
- filtrationThe precipitate was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-f6661dc4b09349f0a087b6dbcf031ff7
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265536B1
Reaction notes
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