Water → 1-(3-Fluoropyridin-2-yl)-3-oxocyclobutane-1-carbonitrile

HRID 869210Notes

Reaction equation

HRID 869210 reaction equation
[F:1][C:2]1[C:3]([C:8]2([C:13]#[N:14])[CH2:11][C:10](=C)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH2:15]>C(Cl)Cl.C(#N)C>[F:1][C:2]1[C:3]([C:8]2([C:13]#[N:14])[CH2:11][C:10](=[O:15])[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 674510301-(3-Fluoropyridin-2-yl)-3-methylenecyclobutane-1-carbonitrile

Product 1

HCID 674531411-(3-Fluoropyridin-2-yl)-3-oxocyclobutane-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

To a mixture of 1-(3-fluoropyridin-2-yl)-3-methylenecyclobutanecarbonitrile (272 g, 1.45 mol) and RuCl3.H2O (9.0 g, 0.044 mol) in DCM (1 L), acetonitrile (1 L), and water (1.5 L) was added solid NaIO4 (1235 g, 5.8 mol) portionwise at 10-30° C. Upon completion of the addition, the reaction was stirred 1 h at 15° C. and overnight at rt. The solid precipitate was filtered off and washed with DCM (1 L×2). The organic layer was washed with water (500 mL×2) and brine (500 mL), dried over Na2SO4, and concentrated to provide the title compound as a crude dark solid (238 g, 86.3%), LRMS (M+H+) m/z 191.1.

Workup

  1. additionUpon completion of the addition
  2. filtrationThe solid precipitate was filtered off
  3. washwashed with DCM (1 L×2)
  4. washThe organic layer was washed with water (500 mL×2) and brine (500 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9a2f384fdaee4231ba5960574d0d8bda
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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