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

HRID 1245166
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HRID 1245166 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:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9](OS(C(F)(F)F)(=O)=O)[CH:8]=1.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:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([C:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)[CH:8]=1
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참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 11237521Methyl 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate

생성물 1

HCID 21919158Methyl 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoate수율 99.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
95 °C

실험 절차

To a solution of methyl 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate (333 mg, 0.6555 mmol) in toluene (6 ml) were added tetrakistriphenylphosphine palladium (23 mg, 0.0199 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 1.00 ml), lithium chloride (56 mg, 1.3241 mmol) and ethanolic solution (1.3 ml) of pyridine-3-boronic acid 1,3-propanediol cyclic ester (159 mg, 0.9814 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=1:1) to give the title compound (284 mg, 0.6498 mmol, 99%).

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-7b6c9ea3ae8f47a6a1218c824c09437c
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07122543B2

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