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Triethylamine → 4-[5-[4-(6-Methoxyhexyloxy)phenyl]isoxazol-3-yl]benzoic acid methyl ester

HRID 1816689
Notes
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Reaction equation

HRID 1816689 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].[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])=[CH:19][CH:18]=1)#[CH:16].C(N(CC)CC)C>O1CCCC1.ClCCl>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])=[CH:19][CH:18]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 224946961-Ethynyl-4-(6-methoxyhexyloxy)benzeneHCID 73989494alpha-Chloro-4-methoxycarbonylbenzaldoxime

Product 1

HCID 543928284-[5-[4-(6-Methoxyhexyloxy)phenyl]isoxazol-3-yl]benzoic acid methyl esterYield 73.3%

Reagents, catalysts & solvents 2

HCID 6344Dichloromethane
Solvent
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 4-methoxycarbonylphenylhydroxyiminomethyl chloride (975 mg) and 1-ethynyl-4-(6-methoxyhexyloxy)benzene (1.06 g) in tetrahydrofuran (10 ml) was added triethylamine (0.83 ml) in tetrahydrofuran (10 ml) over a period of 30 minutes at 40° C., and the mixture was stirred at 40° C. for 3 hours and 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 4-[5-[4-(6-methoxyhexyloxy)phenyl]isoxazol-3-yl]benzoic acid methyl ester (1.37 g).

Workup

  1. washwashed with water and brine
  2. dry with materialThe separated organic layer was dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was triturated with acetonitrile
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-5e230c76fefc4caa8c269cf774251b70
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06884868B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes