Dimethylformamide → 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carboxaldehyde
Reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][CH2:7][C:8]1[S:9][CH:10]=[C:11]([CH3:13])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.CN(C)[CH:29]=[O:30]>>[Si:5]([O:6][CH2:7][C:8]1[S:9][C:10]([CH:29]=[O:30])=[C:11]([CH3:13])[CH:12]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:15])[CH3:14]Participants
5
Procedure
The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 10 (10b) using t-butyl(dimethyl) [(4-methyl-2-thienyl)methoxy]silane (2.5 g, 10 mmol) that was obtained in Example 11 (11a), 1.6 M solution of n-butyllithium in hexane (7.8 mL, 12 mmol), and N,N-dimethylformamide (1.6 mL, 21 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 (0:10 to 5:95) as the eluent to afford the title compound (2.5 g) in a yield of 89% as a pale yellowish oily product.
Workup
- customthe reaction similar to
Sources & evidence
- ORD record
- ord-aba5069eb0bd4d1191252cf986e32741
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
Loading…