Vinyl Acetate → HCID 54446963, compound

HRID 2260105Notes

Reaction equation

HRID 2260105 reaction equation
O([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)S(C(F)(F)F)(=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38]([O:41][CH:42]=[CH2:43])(=[O:40])[CH3:39]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:38]([O:41][CH:42]=[CH:43][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)(=[O:40])[CH3:39]

Participants

6

Reactant 3

HCID 7904Vinyl AcetateHCID 11776TriphenylphosphineHCID 45463412-Naphthyl Trifluoromethanesulfonate

Product 1

HCID 54446963HCID 54446963, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-naphthyl triflate (90 g, 326 mmol) in DMF (240 ml), add triphenylphosphine (9.6 g, 36.6 mmol), vinyl acetate (149 g, 1862 mmol) and palladium acetate (3.8 g, 17 mmol). Reflux the reaction mixture for 1 h, then quench by addition of sat'd NaHCO3 solution. Extract the mixture with Et2O, dry and concentrate. Purify the residue by chromatography on silica gel (5% EtOAc in hexane) to obtain 35 g (165 mmol, 51%) 2-(2-naphthyl)vinyl acetate.

Workup

  1. temperatureReflux the reaction mixture for 1 h
  2. customquench by addition of sat'd NaHCO3 solution
  3. extractionExtract the mixture with Et2O
  4. customdry
  5. concentrationconcentrate
  6. customPurify the residue by chromatography on silica gel (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-4ba9814a443c42e49d0c334f0d7a8f0e
Source dataset
uspto-grants-1995_12
Patent number
US05476847

Reaction notes

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