Potassium Cyanide → HCID 22602339, compound

HRID 2308392Notes

Reaction equation

HRID 2308392 reaction equation
Br[CH2:2][CH2:3]/[CH:4]=[C:5](\[CH3:15])/[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C-:16]#[N:17].[K+]>CN(C=O)C.O>[CH3:15]/[C:5](/[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4]\[CH2:3][CH2:2][C:16]#[N:17]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 22602328HCID 22602328, compound

Product 1

HCID 22602339HCID 22602339, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of the (E)-1-bromo-4-methyl-3-tridecene (3) (38.0 g, 138 mmols) and KCN (11.5 g, 176 mmols) in DMF (100 ml) and water (30 ml) was stirred for 24 hours at 70° C. Then, the mixture was poured into ice water (1 L) and extracted with ether (500 ml). The ether solution was washed with water, dried (MgSO4), and concentrated in a vacuum. The residue was subjected to silica gel chromatography, and eluted with n-hexane-ether (100:1) to obtain 30.0 g (98%) of (E)-5-methyl-4-tetradecenenitrile (4) as oily matter.

Workup

  1. extractionextracted with ether (500 ml)
  2. washThe ether solution was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in a vacuum
  5. washeluted with n-hexane-ether (100:1)

Sources & evidence

ORD record
ord-65caf914a0ee402bbf51d1d3751588e1
Source dataset
uspto-grants-2004_12
Patent number
US06835846B2

Reaction notes

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