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Sodium Carbonate → HCID 21919179, compound

HRID 1245170
Notes
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Reaction equation

HRID 1245170 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][C:7]1[CH:8]=[CH:9][C:10](OS(C(F)(F)F)(=O)=O)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+].[CH3:43][O:44][C:45]1[CH:50]=[CH:49][C:48](B(O)O)=[CH:47][CH:46]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[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:7]1[CH:8]=[CH:9][C:10]([C:48]2[CH:49]=[CH:50][C:45]([O:44][CH3:43])=[CH:46][CH:47]=2)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 433294Lithium ChlorideHCID 21919171HCID 21919171, compound

Product 1

HCID 21919179HCID 21919179, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate (411 mg, 0.8090 mmol) in toluene (12 ml) were added tetrakistriphenylphosphine palladium (60 mg, 0.0519 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 1.35 ml), lithium chloride (89 mg, 2.0995 mmol) and ethanolic solution (2.0 ml) of 4-methoxybenzene boronic acid (369 mg, 2.4282 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=5:1) to give the title compound (351 mg, 0.7532 mmol, 93%).

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=5:1)

Sources & evidence

ORD record
ord-c625f7ab0ceb4c968d690937cd56ae7f
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