Potassium Carbonate → HCID 67465898, compound

HRID 2171159Notes

Reaction equation

HRID 2171159 reaction equation
[OH:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1>C(#N)C>[CH3:21][O:20][C:3]1[C:2]([O:1][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][CH:35]=2)=[C:7]([O:8][CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[O:14][CH2:13]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27335814-(Methylsulfonyl)benzyl BromideHCID 674677565-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one

Product 1

HCID 67465898HCID 67465898, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 5-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one (80 mg, 0.279 mmol) in acetonitrile (10 mL) was added potassium carbonate (115 mg, 0.837 mmol) and 1-(bromomethyl)-4-(methylsulfonyl)benzene (208 mg, 0.837 mmol) and the resultant reaction mixture was heated to 80° C. for 4 h. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, 0-50% ethyl acetate in pet ether) to afford the title compound as a solid (25 mg, 19.7%).

Workup

  1. customthe resultant reaction mixture
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by column chromatography (silica gel, 0-50% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-d580630d93ae41d39fa5e3bac795367e
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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