Methyl iodide → 1-(4-Methoxybut-1-ynyl)-2-nitrobenzene
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][CH2:12][CH2:13][OH:14])([O-:3])=[O:2].[CH3:15]I>C(#N)C.[Ag]=O>[CH3:15][O:14][CH2:13][CH2:12][C:11]#[C:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A solution of 2.9 g of 4-(2-nitrophenyl)but-3-yn-1-ol in 750 ml of acetonitrile is admixed at room temperature with 17.5 g of silver oxide and 9.4 ml of methyl iodide and stirred at 50° C. over 70 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.34 (1:2 EtOAc-heptane); Rt=4.17.
Workup
- filtrationThe reaction mixture is clarified by filtration
- concentrationthe filtrate is concentrated by evaporation
Sources & evidence
- ORD record
- ord-186d4a82c9e544948855a8c27cebc110
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842688B2
Reaction notes
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