Dimethyl Sulfoxide → Methyl 5-(2-methoxyethoxy)-4'-methylbiphenyl-3-carboxylate

HRID 1845277노트

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HRID 1845277 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.Br[CH2:20][CH2:21][O:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>CCOC(C)=O>[CH3:23][O:22][CH2:21][CH2:20][O:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[CH:7]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

생성물 1

HCID 58188233Methyl 5-(2-methoxyethoxy)-4'-methylbiphenyl-3-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
135 °C

실험 절차

A mixture of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (400 mg, 1.65 mmol), 1-bromo-2-methoxyethane (436 mg, 3.14 mmol), potassium carbonate (434 mg, 3.14 mmol), and dimethyl sulfoxide (5 mL) was stirred at 135° C. overnight. After cooling, the mixture was diluted with EtOAc and washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (0-100% EtOAc/hexane) to afford the title compound.

후처리

  1. temperatureAfter cooling
  2. washwashed with aq. NaHCO3 (sat.)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (0-100% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-72a93605b4bd49e4b469d64dfc20347a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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