Triethylamine → HCID 18756282, compound

HRID 434033

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]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 138378Phenylpropynoic acid methyl esterHCID 71367044HCID 71367044, compound

Product 1

HCID 18756282HCID 18756282, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

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
Patent number
US06670373B1

Linked notes

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