Triethylamine → 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carbonitrile
Reaction equation
[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([CH:15]=O)=[C:12]([CH3:17])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.NO.C([N:23](CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15]#[N:23])=[C:12]([CH3:17])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
5
Procedure
The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 10 (10c) using 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carboxaldehyde (2.5 g, 9.2 mmol) that was obtained in Example 11 (11b), hydroxylamine hydrochloride (0.71 g, 10 mmol), triethylamine (2.6 mL, 18 mmol), and N,N′-dicyclohexylcarbodiimide (2.1 g, 10 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 100% as a pale yellowish oily product.
Workup
- customthe reaction similar to
Sources & evidence
- ORD record
- ord-51485fbdc89d47dcb6de507a8977477b
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
Loading…