Sodium Cyanide → 4-(1,3-dioxolan-2-yl)-4-methylpentanenitrile

HRID 2117718Notes

Reaction equation

HRID 2117718 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([CH:8]1[O:12][CH2:11][CH2:10][O:9]1)([CH3:7])[CH3:6].[C-]#[N:14].[Na+]>CS(C)=O.O>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:5]([CH3:7])([CH3:6])[CH2:4][CH2:3][C:2]#[N:14]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 229963392-(5-Chloro-2-methylpentan-2-yl)-1,3-dioxolane

Product 1

HCID 2992134-(1,3-dioxolan-2-yl)-4-methylpentanenitrileYield 107.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

0.74 g (3.8 mmol) of 2-(4-chloro-1,1-dimethylbutyl)-1,3-dioxolane) and 0.50 g (7.7 mmol) of sodium cyanide in 5 mL of DMSO was heated to 100° C. with stirring. After 18 hours the solution was cooled to RT, diluted with water, and the mixture extracted with ether (3×). The combined ether extracts were washed with water. (3×), dried over MgSO4, and concentrated in vacuo to afford 0.69 g (90%) of the desired compound as a light yellow liquid.

Workup

  1. extractionthe mixture extracted with ether (3×)
  2. washThe combined ether extracts were washed with water
  3. dry with material(3×), dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-013a5a99911f442fb36f0a9b975f00a9
Source dataset
uspto-grants-2008_10
Patent number
US07442718B2

Reaction notes

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