Quinone → HCID 59684264, compound

HRID 602274Notes

Reaction equation

HRID 602274 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[O:29][CH3:30].C1(=O)C=CC(=O)C=C1>C1COCC1.C(OCC)(=O)C.CC#N.CC#N.Cl[Pd]Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:13][C:12](=[O:14])[C:11]3[C:10]([CH:9]=2)=[CH:18][CH:17]=[C:16]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH:15]=3)=[CH:4][C:3]=1[O:29][CH3:30]

Participants

6

Reactant 2

HCID 4650QuinoneHCID 59684231HCID 59684231, compound

Product 1

HCID 59684264HCID 59684264, compoundYield 50.3%

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-2-[2-(4-fluoro-3-methoxyphenyl)vinyl]-5-(4-methoxybenzyloxy)benzoic acid (600 mg, 1.47 mmol) in anhydrous THF (5 mL) was sparged with nitrogen for 5 min, then PdCl2(MeCN)2 (39 mg, 0.15 mmol), p-benzoquinone (175 mg, 1.62 mmol), and molecular sieves (10 mg) were added and the mixture stirred at room temperature for 24 h. The reaction mixture was diluted with ethyl acetate and washed with 1 N NaOH (aq.). The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was purified by chromatography on silica gel with hexanes:EtOAc (2:1, v/v) as eluent to afford 3-(4-fluoro-3-methoxyphenyl)-7-(4-methoxybenzyloxy)isochromen-1-one (300 mg, 0.74 mmol, 50%).

Workup

  1. washwashed with 1 N NaOH (aq.)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by chromatography on silica gel with hexanes:EtOAc (2:1

Sources & evidence

ORD record
ord-faea881d47cf4248b6c089a89d2996a1
Source dataset
uspto-grants-2011_03
Patent number
US07906504B2

Reaction notes

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