2-Trimethylsilyloxy-4-(4-(methylthio)phenyl)-3,4-dihydrofuran → 4-(4-(methylthio)phenyl)-2-(5H)-furanone

HRID 1376583Notes

Reaction equation

HRID 1376583 reaction equation
C[Si](C)(C)[O:3][CH:4]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=2)[CH2:6][O:5]1>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:16][S:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[CH2:6][O:5][C:4](=[O:3])[CH:8]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 184001922-Trimethylsilyloxy-4-(4-(methylthio)phenyl)-3,4-dihydrofuran

Product 1

HCID 121505894-(4-(methylthio)phenyl)-2-(5H)-furanone

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4 g of Pd(OAc)2 in 100 mL of acetonitrile is added dropwise the crude product from Step 1 (5 g) under nitrogen at r.t. After 10 h at r.t., the mixture is condensed under reduced pressure and the residue is purified by flash chromatography on silica gel eluted with 2:1 hexane/EtOAc to give the title compound.

Workup

  1. customcondensed under reduced pressure
  2. customthe residue is purified by flash chromatography on silica gel
  3. washeluted with 2:1 hexane/EtOAc

Sources & evidence

ORD record
ord-1b96c830b698475094f3555bb5994cd8
Source dataset
uspto-grants-1997_09
Patent number
US05663195

Reaction notes

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