Diethyl Ether → 2(5H)-Furanone, 4-[4-(methylthio)phenyl]-3-phenyl-

HRID 1107884Notes

Reaction equation

HRID 1107884 reaction equation
I[C:2]1[C:3](=[O:15])[O:4][CH2:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[As](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>C1C=CC=CC=1.[OH-].[Na+]>[C:16]1([C:2]2[C:3](=[O:15])[O:4][CH2:5][C:6]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11773TriphenylarsineHCID 66827Phenylboronic AcidHCID 121505903-iodo-4-(4-(methylthio)phenyl)-2-(5H)-furanone

Product 1

HCID 110442352(5H)-Furanone, 4-[4-(methylthio)phenyl]-3-phenyl-

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4 g of the product of Step 3, 3.7 g of PhB(OH)2, 0.4 g of Ph3As, 0.4 g of PdCl2 (PhCN)2 in 100 mL of benzene and 15 mL of 2N NaOH is refluxed for 6 h. After cooling to r.t., Et2O (200 mL) is added to the reaction mixture and the mixture is washed with 100 mL of saturated NaHCO3. The organic layer is dried over MgSO4 and concentrated. The residue is purified by flash chromatography on silica gel eluted with 4:1 hexane/EtOAc to give the title compound.

Workup

  1. temperatureis refluxed for 6 h
  2. washthe mixture is washed with 100 mL of saturated NaHCO3
  3. dry with materialThe organic layer is dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography on silica gel
  6. washeluted with 4:1 hexane/EtOAc

Sources & evidence

ORD record
ord-e443f5026e834a07b7d922226dffc299
Source dataset
uspto-grants-2000_05
Patent number
US06063811

Reaction notes

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