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

HRID 1245167노트

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HRID 1245167 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
95 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-df42afa5fa594bc2a5d3f031aa195b4e
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122543B2

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