1,4-Dioxane → HCID 66824419, compound

HRID 1966151Notes

Reaction equation

HRID 1966151 reaction equation
[O:1]1[CH2:6][CH2:5]OCC1.[F:7][CH2:8][C:9]1([C:14]#[N:15])CC(=C)[CH2:10]1.I([O-])(=O)(=O)=O.[Na+]>O.[Os](=O)(=O)(=O)=O>[F:7][CH2:8][C:9]1([C:14]#[N:15])[CH2:5][C:6](=[O:1])[CH2:10]1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 23667635Sodium periodateHCID 66824431HCID 66824431, compound

Product 1

HCID 66824419HCID 66824419, compound

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-(fluoromethyl)-3-methylenecyclobutanecarbonitrile (0.256 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 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 materialwere dried over MgSO4
  4. customAfter removal of the solvents

Sources & evidence

ORD record
ord-323017bfa935455c8c2f6c67991c1f39
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

Loading…