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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2202589Generated: October 31, 2026

Trimethylsilyl cyanide → 4-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile

https://huagongshe.com/reaction/2202589

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrimethylsilyl cyanideHCID 82115—
Reactant4-(tert-Butyldimethylsilanyloxymethyl)pyridine 1-oxideHCID 21781515—
SolventTriethylamineHCID 8471—
Product4-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrileHCID 1454144820.9%

Reaction Conditions

Temperature90 °C

Reaction Steps

Under a nitrogen atmosphere, 4-(tert-butyldimethylsilyloxymethyl)pyridine-1-oxide (1.2 g, 5 mmol) synthesized in Production Example 85 was dissolved in triethylamine, and trimethylsilylcyanide (744 μL, 6 mmol) was added thereto. The mixture was stirred at 90° C. for 3 hours. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature. The solvent was distilled off. The resulting residue was dissolved in ethyl acetate and washed with water 3 times and with a saturated saline solution once. Thereafter, the organic layer was dried over magnesium sulfate. The solvent was distilled off, and thus the title compound (260 mg, 20.9%) was obtained as an oily substance.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365553B2
Source datasetuspto-grants-2016_06
ORD IDord-7a558f90d73d4f72935692b0689fd72e
Source noteuspto-grants-2016_06