Potassium Carbonate → 3-Methyl-3-naphthalen-1-ylmethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 523515Notes

Reaction equation

HRID 523515 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)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[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]([CH3:15])([CH2:14][C:31]3[C:32]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:28]=[CH:29][CH:30]=3)[CH2:12][O:11][C:6]=2[CH:5]=1)=[O:16]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 251290454-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester

Product 1

HCID 684828853-Methyl-3-naphthalen-1-ylmethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterYield 43%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (455 mg, 1.37 mmol) 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 1-Naphthylboronic acid, (282 mg, 1.64 mmol) was submitted to microwave irradiation at 100° C. for 10 minutes and as the reaction was not completed at 150° C. for 15 minutes. The resulting mixture was filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded 196 mg (43%) of the title compound as a slightly brown oil.

Workup

  1. customirradiation at 100° C. for 10 minutes
  2. filtrationThe resulting mixture was filtered over silica
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c16f71b674f84cfd9a8d0a644e7f78dd
Source dataset
uspto-grants-2016_05
Patent number
US09339486B2

Reaction notes

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