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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2247693Generated: October 29, 2026

Triethylamine → 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carbonitrile

https://huagongshe.com/reaction/2247693

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantDicyclohexylcarbodiimideHCID 10868—
ReactantHydroxyamine hydrochlorideHCID 443297—
Reactant5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carboxaldehydeHCID 86620221—
Product5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carbonitrileHCID 68528449—

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07687491B2
Source datasetuspto-grants-2010_03
ORD IDord-51485fbdc89d47dcb6de507a8977477b
Source noteuspto-grants-2010_03