Triethylamine → 4-{[t-Butyl(dimethyl)silyl]oxy}-4,5,6,7-tetrahydro-1-benzofuran-2-carbonitrile
Reaction equation
[Si:1]([O:8][CH:9]1[C:14]2[CH:15]=[C:16]([CH:18]=O)[O:17][C:13]=2[CH2:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.NO.C([N:25](CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[Si:1]([O:8][CH:9]1[C:14]2[CH:15]=[C:16]([C:18]#[N:25])[O:17][C:13]=2[CH2:12][CH2:11][CH2:10]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 similar reaction to that mentioned in Example 1 (1c) using 4-{[t-butyl(dimethyl)silyl]oxy}-4,5,6,7-tetrahydro-1-benzofuran-2-carboxaldehyde (4.3 g, 15.3 mmol) that was obtained in Example 7 (7b), hydroxylamine hydrochloride (1.2 g, 17 mmol), triethylamine (4.3 ml, 31 mmol), and N,N′-dicyclohexylcarbodiimide (3.5 g, 17 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 (1:9) as the eluent to afford the title compound (3.0 g) in a yield of 71% as a colourless oily product.
Workup
- customthe similar reaction to
Sources & evidence
- ORD record
- ord-8f733bf47e094054b4011aeccff3f0c6
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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