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Triethylamine → 4-Methoxycarbonyl-5-phenyl-3-(2-chloro-6-fluorophenyl)isoxazole

HRID 434033
Notes
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Reaction equation

HRID 434033 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[C:4](=[N:6][OH:7])Cl.[CH3:13][O:14][C:15](=[O:24])[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>CCOCC.O>[CH3:13][O:14][C:15]([C:16]1[C:4]([C:3]2[C:8]([F:12])=[CH:9][CH:10]=[CH:11][C:2]=2[Cl:1])=[N:6][O:7][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 138378Phenylpropynoic acid methyl esterHCID 713670442-chloro-6-fluoro-N-hydroxybenzimidoyl chloride

Product 1

HCID 187562824-Methoxycarbonyl-5-phenyl-3-(2-chloro-6-fluorophenyl)isoxazoleYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 3283
Diethyl Ether
Solvent
3×

Procedure

To a solution of 2-chloro-6-fluorobenzoylchloride oxime (1.04 g, 5.00 mmol) and methyl-3-phenyl-2-propynoate (1.20 g, 7.50 mmol) in Et2O (25 ml) at 0° C. under nitrogen was added a solution of triethyl amine (0.834 ml, 6.00 mmol) in Et2O (3 ml) over 1 h. The reaction was allowed to warm to room temperature overnight (17 h). The mixture was diluted with Et2O and H2O, the layers separated, and the organic fraction was dried (MgSO4). Column chromatography (silica gel, hexane/Et2O gradient) gave the title compound (1.53 g, 92%).

Workup

  1. customthe layers separated
  2. dry with materialthe organic fraction was dried (MgSO4)

Sources & evidence

ORD record
ord-438d114149954189898f47939d083395
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06670373B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes