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Potassium Carbonate → 5-(4-Ethoxy-3-methoxy-2-(4-(methylsulfonyl)benzyloxy)phenyl)isobenzofuran-1(3H)-one

HRID 2171139
Notes
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Reaction equation

HRID 2171139 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([OH:20])[C:5]=1[O:21][CH3:22])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(#N)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([O:20][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:35][CH:36]=2)[C:5]=1[O:21][CH3:22])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27335814-(Methylsulfonyl)benzyl BromideHCID 701700835-(4-Ethoxy-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one

Product 1

HCID 701701335-(4-Ethoxy-3-methoxy-2-(4-(methylsulfonyl)benzyloxy)phenyl)isobenzofuran-1(3H)-oneYield 16%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 5-(4-ethoxy-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one (80 mg, 0.266 mmol) in acetonitrile (7 mL) was added potassium carbonate (110 mg, 0.80 mmol) and 1-(bromomethyl)-4-(methylsulfonyl)benzene (99 mg, 0.399 mmol) and the resultant reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 0-40% ethyl acetate in pet ether) afforded title compound as a solid (20 mg, 16%).

Workup

  1. customthe resultant reaction mixture
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification of the residue by flash column chromatography (silica gel, 0-40% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-e64958a5779f40c18116171b6c32304a
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09051290B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes