Triethylamine → Methyl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoate

HRID 1872402

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

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-b78335e158dd48b8bd5da9f7ec3aed03
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06107458

Linked notes

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