Potassium Cyanide → HCID 10634316, compound

HRID 1816005Notes

Reaction equation

HRID 1816005 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[C-:9]#[N:10].[K+].[CH3:12][C:13]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CC#N.[Zn+2].[I-].[I-]>[Si:16]([O:8][CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:9]#[N:10])([C:13]([CH3:15])([CH3:14])[CH3:12])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 103713-PyridinecarboxaldehydeHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10634316HCID 10634316, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-pyridinecarboxaldehyde (1.0 g, 9.34 mmole) in CH3CN (45 mL) was added KCN (6.0 g, 93 mmole), TBDMSCl (1.7 g, 11.21 mmole), and ZnI2 (50 mg, 0.16 mmole). After 4 hr at RT the mixture was filtered through celite® and the filtrate was concentrated. Flash chromatography on silica gel (25% EtOAc/hexanes) gave the title compound (2.17 g. 94%) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 8.63-8.73 (m, 2 H), 7.80-7.87 (m, 1 H), 7.33-7.41 (m, 1 H), 5.57 (s, 1 H), 0.97 (s, 9 H), 0.27 (s, 3 H), 0.19 (s, 3 H).

Workup

  1. filtrationAfter 4 hr at RT the mixture was filtered through celite®
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9a54016e0f6d45b9bbbec12bc7b6737e
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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