HCID 54348134, compound → HCID 72609440, compound

HRID 1595207Notes

Reaction equation

HRID 1595207 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)[CH3:7])[C:2]#[CH:3].[CH3:18][O:19][C:20](=[O:26])[C:21](Br)=[CH:22][O:23][CH3:24]>C(N(CC)CC)C.O1CCCC1.[Cu]I>[CH3:18][O:19][C:20](=[O:26])[C:21](=[CH:22][O:23][CH3:24])[C:3]#[C:2][CH2:1][O:4][N:5]=[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=1)[CH3:7]

Participants

6

Reactant 2

HCID 54348134HCID 54348134, compoundHCID 54395891HCID 54395891, compound

Product 1

HCID 72609440HCID 72609440, compoundYield 31.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

0.25 g of Pd(TPP)2Cl2 and also 0.1 g of copper(I) iodide are added, under an argon atmosphere, to a solution of 10.0 g of 1-(3-trifluoromethylphenyl)ethanone O-prop-2-ynyl-oxime in 150 ml of triethylamine and the mixture is heated to 70° C. 8.9 g of 2-bromo-3-methoxyacrylic acid methyl ester in 30 ml of tetrahydrofuran are then added and the mixture is stirred at 70° C. for 14 h and then filtered. The filtrate is concentrated by evaporation and chromatographed on silica gel (hexane/diethyl ether 2:1) to yield 4.6 g of the product having a melting point of 57-58° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated by evaporation
  3. customchromatographed on silica gel (hexane/diethyl ether 2:1)

Sources & evidence

ORD record
ord-60954ac2204240f0b3d0ce0d1703c320
Source dataset
uspto-grants-2001_09
Patent number
US06288071B1

Reaction notes

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