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Potassium Carbonate → 3-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 1053714
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HRID 1053714 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7](I)=[C:6]([O:11][CH2:12][C:13]([CH3:15])=[CH2:14])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[C:13]([CH2:15][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([CH3:14])[CH2:12][O:11][C:6]=2[CH:5]=1)=[O:16]
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7

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 251290454-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester

생성물 1

HCID 251290463-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester수율 95.1%

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매
HCID 167845
palladium(II) acetate
촉매
HCID 6228Dimethylformamide용매2회

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온도
115 °C

실험 절차

To a solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (455 mg, 1.37 mmol) obtained in Example 4(A), in DMF (15 mL) were added Potassium carbonate (379 mg, 2.74 mmol), Tetrabutylammonium chloride (380 mg, 1.37 mmol), Palladium acetate (25.6 mg, 0.136 mmol) in DMF (5 mL) and Phenylboronic acid (200 mg, 1.64 mmol). The resulting mixture was stirred for 3 h at 115° C., cooled to room temperature, filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded 368 mg (95%) of the title compound as a slightly brown oil which crystallize. Mp:52° C.

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltered over silica
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a2c6a00584fe424f84a247bb3381f245
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394267B2

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