Reaction equation
[CH3:1][C:2]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14]C)[N:11]=[C:10]([CH2:16][CH2:17][CH2:18]O)[CH:9]=1)([CH3:4])[CH3:3].N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O>ClCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C:8]1[CH:9]=[C:10]2[N:11]([CH2:18][CH2:17][CH2:16]2)[C:12](=[O:14])[CH:13]=1)([CH3:4])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-1-propanol (5.16 g, 16.59 mmol) in dichloromethane (250 ml) was treated with pyridine (2.94 ml, 36.47 mmol) and trifluoromethanesulfonic anhydride (3.1 ml, 19.88 mmol) and stirred at room temperature for 10 min before being treated with tetrabutylammonium iodide (30.61 g, 82.95 mmol) and stirred at room temperature for a further 4 h. Water was then added and the mixture was extracted three times with diethyl ether and the combined organic extracts washed again with water. The organic extracts were dried with magnesium sulphate and evaporated. The residue was chromatographed on silica eluting with 0-10% methanol in dichloromethane to give the desired product (3.93 g, 14.09 mmol)
Workup
- stirringstirred at room temperature for a further 4 h
- extractionthe mixture was extracted three times with diethyl ether
- washthe combined organic extracts washed again with water
- dry with materialThe organic extracts were dried with magnesium sulphate
- customevaporated
- customThe residue was chromatographed on silica eluting with 0-10% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-3cf1578bc419485980131438e0738c79
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732461B2
Linked notes
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