[(5-Bromothiophen-2-yl)methoxy](tert-butyl)dimethylsilane → 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)thiophene-2-carbonitrile
Reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[Cu](C#N)[C:17]#[N:18]>>[Si:9]([O:8][CH2:7][C:5]1[S:6][C:2]([C:17]#[N:18])=[CH:3][CH:4]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]Participants
3
Procedure
The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 3 (3a) using [(5-bromo-2-thienyl)methoxy]t-butyldimethylsilane (2.4 g, 7.8 mmol) [reference literature: Tetrahedron, vol. 39, 2531 (1983)] and copper cyanide (1.3 g, 14 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:50 to 1:7) as the eluent to afford the title compound (1.1 g) in a yield of 56% as a white crystalline solid.
Workup
- customthe similar reaction to
Sources & evidence
- ORD record
- ord-01fb5a0dc34e4a60b6dc5787ba8bfeb7
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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