Cyanide → 2-[2-(1,3-Dioxolan-2-yl)ethyl]cyclohexanone

HRID 849086Notes

Reaction equation

HRID 849086 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]1(C(OC)=O)[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:14].[C-]#N>CS(C)=O.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:14]

Participants

5

Reactant 2

HCID 5975CyanideHCID 18800645Methyl 1-[2-(1,3-dioxolan-2-yl)ethyl]-2-oxocyclohexanecarboxylate

Product 1

HCID 107743392-[2-(1,3-Dioxolan-2-yl)ethyl]cyclohexanone

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The product of Example 102 was reacted with sod ,m cyanide (0.69 g, 14.1 mmoles) in 25 mL of DMSO at 160° C. for 12 hrs. The reaction mixture was then diluted to 700 mL with water and extracted with ethyl acetate/hexane (1:1). The solvent removed from the extracts to provide the title compound as oil.

Workup

  1. extractionextracted with ethyl acetate/hexane (1:1)
  2. customThe solvent removed from the extracts

Sources & evidence

ORD record
ord-1895e359a3e34dcaadeb004c916994e9
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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