Potassium Cyanide → 5-(8-Hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carbonitrile

HRID 1016003Notes

Reaction equation

HRID 1016003 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2([OH:18])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C-:19]#[N:20].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[OH:18][C:8]1([C:5]2[CH:4]=[CH:3][C:2]([C:19]#[N:20])=[N:7][CH:6]=2)[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 595560478-(6-Fluoropyridin-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 667870965-(8-Hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carbonitrileYield 36.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.7 g (6.6 mmol) of 8-(6-fluoropyridin-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol in 20 mL of DMF was added KCN (430 g, 6.6 mmol) and 18-crown-6 ether (1.8 g, 6.6 mmol). The reaction mixture was refluxed for 2 days. Direct chromatography on silica gel afforded the 5-(8-hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carbonitrile (620 mg, 36%): MS (m/e): 261 (M+1)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 days

Sources & evidence

ORD record
ord-4c0ff53ed28d46f198c9dfca51b669b5
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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