Trimethylsilyl cyanide → 4-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile

HRID 2202589Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N+:13]([O-])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([C:21]#[N:22])(C)C>C(N(CC)CC)C>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:21]#[N:22])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

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.

Workup

temperatureto cool down to a room temperature
distillationThe solvent was distilled off
dissolutionThe resulting residue was dissolved in ethyl acetate
washwashed with water 3 times and with a saturated saline solution once
dry with materialThereafter, the organic layer was dried over magnesium sulfate
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-7a558f90d73d4f72935692b0689fd72e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365553B2

Reaction notes

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