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

HRID 1245167ノート

反応式

HRID 1245167 の反応式
[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]=[C:9](OS(C(F)(F)F)(=O)=O)[CH:10]=[C:11]([CH:16]=1)C(OC)=O.[C:35](=[O:38])([O-])[O-:36].[Na+].[Na+].[Cl-].[Li+].[C:43]1(B(O)O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[C:52]1(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:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[C:11]([CH:16]=1)[C:35]([O:36][CH3:52])=[O:38]

参加物

7

反応物 5

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 21919182Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-3-(trifluoromethanesulfonyl)oxybenzoate

生成物 1

HCID 21919110Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-phenylbenzoate収率 68%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

To a solution of methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-3-(trifluoromethanesulfonyl)oxybenzoate (444 mg, 0.8740 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 (2.1 ml) of benzeneboronic acid (320 mg, 2.6244 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 (349 mg, 0.8004 mmol, 68%).

後処理

  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)

出典と根拠

ORDレコード
ord-df42afa5fa594bc2a5d3f031aa195b4e
出典データセット
uspto-grants-2006_10
特許番号
US07122543B2

反応ノート

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