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

HRID 1053726
Notes
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Reaction equation

HRID 1053726 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+].[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1B(O)O>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:25]3[CH:24]=[CH:23][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)[CH2:12][O:11][C:6]=2[CH:5]=1)=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 251290454-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester

Product 1

HCID 684764713-Methyl-3-naphthalen-2-ylmethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterYield 22%

Reagents, catalysts & solvents 3

HCID 70681
Tetrabutylammonium Chloride
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 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 2-Naphthylboronic acid, (282 mg, 1.64 mmol) was submitted to microwave irradiation at 150° C. for 16 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 100 mg (22%) of the title compound as a slightly brown oil which crystallized.

Workup

  1. customirradiation at 150° C. for 16 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-51c802eba6cc45dab5467ec2a96c9b0d
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394267B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes