1,4-Dioxane → 1-(Cyanomethyl)-3-oxocyclobutanecarbonitrile

HRID 1692929Notes

Reaction equation

HRID 1692929 reaction equation
[O:1]1[CH2:6][CH2:5]OCC1.[C:7]([CH2:9][C:10]1([C:15]#[N:16])CC(=C)[CH2:11]1)#[N:8].I([O-])(=O)(=O)=O.[Na+]>O.[Os](=O)(=O)(=O)=O>[C:7]([CH2:9][C:10]1([C:15]#[N:16])[CH2:5][C:6](=[O:1])[CH2:11]1)#[N:8]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 23667635Sodium periodateHCID 668243831-(Cyanomethyl)-3-methylenecyclobutanecarbonitrile

Product 1

HCID 668242591-(Cyanomethyl)-3-oxocyclobutanecarbonitrile

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

A mixture of water (2 mL, 0.1 mol) and 1,4-dioxane (6 mL, 0.08 mol), 1-(cyanomethyl)-3-methylenecyclobutanecarbonitrile (0.270 g, 0.00204 mol), and 0.2 M of osmium tetraoxide in water (0.04 mL) was stirred for 5 min, during which time the mixture became brown. While the temperature was maintained at room temperature, sodium periodate (0.919 g, 0.00430 mol) was added in portions over a period of 30 min. The mixture was stirred overnight. The mixture was extracted with EtOAc and the combined organic layers were dried over MgSO4. After removal of the solvents, the crude product was used directly in next step.

Workup

  1. stirringThe mixture was stirred overnight
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. customAfter removal of the solvents

Sources & evidence

ORD record
ord-fe79569ac285414abe33eb6c5789f867
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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