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Ethyl Acetate → Methyl 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-phenylbenzoate

HRID 1245165
Notes
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Reaction equation

HRID 1245165 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:25]([O:32][CH3:33])=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6]C1C=CC(C(OC)=O)=C(OS(C(F)(F)F)(=O)=O)C=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+].[C:43]1(B(O)O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[C:52]([O:55][CH2:56]C)(=[O:54])[CH3:53]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:25]([O:32][CH3:33])=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6][C:3]1[CH:4]=[CH:5][C:53]([C:52]([O:55][CH3:56])=[O:54])=[C:26]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 11237521Methyl 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate

Product 1

HCID 10113900
Methyl 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-phenylbenzoate
Yield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of methyl 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate (102 mg, 0.2007 mmol) in toluene (2.3 ml) were added tetrakistriphenylphosphine palladium (4.6 mg, 0.0039 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 0.35 ml), lithium chloride (17 mg, 0.4010 mmol) and ethanolic solution (1.0 ml) of benzene boronic acid (27 mg, 0.2214 mmol) and the mixture was heated with stirring at 95° C. for 16 hours. The reaction solution was diluted with ethyl acetate (100 ml), washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to give the title compound (84 mg, 0.1926 mmol, 96%).

Workup

  1. temperaturethe mixture was heated
  2. washwashed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-2444e6585ff74970958c7666de467121
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122543B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes