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Potassium Carbonate → 3-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 1053714
Notes
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Reaction equation

HRID 1053714 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7](I)=[C:6]([O:11][CH2:12][C:13]([CH3:15])=[CH2:14])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[C:13]([CH2:15][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([CH3:14])[CH2:12][O:11][C:6]=2[CH:5]=1)=[O:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 251290454-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester

Product 1

HCID 251290463-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterYield 95.1%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium Chloride
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
115 °C

Procedure

To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (455 mg, 1.37 mmol) obtained in Example 4(A), in DMF (15 mL) were added Potassium carbonate (379 mg, 2.74 mmol), Tetrabutylammonium chloride (380 mg, 1.37 mmol), Palladium acetate (25.6 mg, 0.136 mmol) in DMF (5 mL) and Phenylboronic acid (200 mg, 1.64 mmol). The resulting mixture was stirred for 3 h at 115° C., cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded 368 mg (95%) of the title compound as a slightly brown oil which crystallize. Mp:52° C.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered over silica
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a2c6a00584fe424f84a247bb3381f245
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394267B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes