Potassium Cyanide → HCID 55267639, compound

HRID 2108378Notes

Reaction equation

HRID 2108378 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1.[C-:10]#[N:11].[K+].C1OCCOCCOCCOCCOCCOC1.C(P(CCCC)CCCC)CCC>C(#N)C.O>[C:10]([CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1)#[N:11]

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 13831TributylphosphineHCID 2855718-Crown-6HCID 9942144(2-Methylpyridin-4-yl)methanol

Product 1

HCID 55267639HCID 55267639, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred mixture of 4-hydroxymethyl-2-methyl-pyridine [CAS No. 105250-16-6] (3.37 g, 27.4 mmol), potassium cyanide (3.56 g, 54.7 mmol) and 18-crown-6 (0.72 g, 2.74 mmol) in acetonitrile (75 ml) was added dropwise at 15-20° C. a solution of tributylphosphine (7.16 g, 30.1 mmol) in acetonitrile (25 ml). The reaction mixture was stirred at room temperature for 25 h, poured into water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water (3×100 ml), brine (100 ml) dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate) to yield 4-cyanomethyl-2-methyl-pyridine (2.26 g, 62%) as a brown oil.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined organic layers were washed with water (3×100 ml), brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-7ead5c03280c4ee8b50d8aac11accd9d
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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