Potassium Cyanide → 6-Cyano-4-chromanone

HRID 32048Notes

Reaction equation

HRID 32048 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:17])[CH2:12][CH2:13][O:14]2)=[CH:9][CH:8]=1)(=O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-:39]#[N:40].[K+]>CC#N.Cl.O.CC(C)=O.CCOCC.[Zn]>[C:39]([C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:17])[CH2:12][CH2:13][O:14]2)=[CH:9][CH:8]=1)#[N:40]

Participants

10

Reactant 3

HCID 9032Potassium CyanideHCID 11776TriphenylphosphineHCID 103571863,4-Dihydro-4-oxo-2H-1-benzopyran-7-yl 1,1,1-trifluoromethanesulfonate

Product 1

HCID 223499736-Cyano-4-chromanone

Reagents, catalysts & solvents 6

HCID 23994ZincCatalystHCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

7-[[(Trifluoromethyl)sulfonyl]oxy]-4-chromanone (27.8 g, 94 mmol) and PPh3 (2.5 g, 9.6 mmol) were dissolved in degassed CH3CN (350 mL). KCN (6.8 g, 105 mmol), (PPh3)2NiBr2 (3.5 g, 4.7 mmol) and acid washed (stirred in 0.5 N HCl 1 min, washed successively with H2O, acetone, and Et2O) zinc dust (2.0 g, 31 mmol) were added and the reaction was purged with N2. The reaction was heated in a 60° C. bath for 6 h. The reaction was cooled, poured into H2O (400 mL) and extracted with EtOAc (3×300 mL). The organic layers were combined and washed with H2O (200 mL) and brine (150 mL). The solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified on a plug of silica (CH2Cl2 eluant) to provide the title compound.

Workup

  1. additionwere added
  2. customthe reaction was purged with N2
  3. temperatureThe reaction was cooled
  4. additionpoured into H2O (400 mL)
  5. extractionextracted with EtOAc (3×300 mL)
  6. washwashed with H2O (200 mL) and brine (150 mL)
  7. dry with materialThe solution was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide a residue which
  11. customwas purified on a plug of silica (CH2Cl2 eluant)

Sources & evidence

ORD record
ord-20a185771eb5486287876b67eca5b738
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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