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Sodium Carbonate → Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoate

HRID 1245168
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HRID 1245168 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]=[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+].B1([C:49]2[CH:54]=[CH:53][CH:52]=[N:51][CH:50]=2)OCCCO1>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:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13]
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참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 21919171HCID 21919171, 화합물

생성물 1

HCID 21919126Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoate수율 98%

시약·촉매·용매 2

HCID 1140
Toluene
용매
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)-2-(trifluoromethanesulfonyl)oxybenzoate (1.43 g, 2.8149 mmol) in toluene (32 ml) were added tetrakistriphenylphosphine palladium (98 mg, 0.0848 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 3.66 ml), lithium chloride (239 mg, 5.6381 mmol) and ethanolic solution (5.9 ml) of pyridine-3-boronic acid 1,3-propanediol cyclic ester (684 mg, 4.2222 mmol) and the mixture was heated with stirring at 95° C. for 16 hours. The reaction solution was diluted with ethyl acetate (200 ml), washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (1.20 g, 2.7459 mmol, 98%).

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=1:1)

출처 및 근거

ORD 기록
ord-6eff5ad309f6484cb8e2dfd761a059cb
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07122543B2

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