Dimethyl Sulfoxide → Methyl 5-(4-hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylate

HRID 1845325노트

반응식

HRID 1845325 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.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[CH:29]12[O:34][CH:33]1[CH2:32][O:31][CH2:30]2>CCOC(C)=O>[OH:34][CH:29]1[CH2:30][O:31][CH2:32][CH:33]1[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 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

생성물 1

HCID 58188331Methyl 5-(4-hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

A stirred mixture of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (370 mg, 1.4 mmol), potassium carbonate (421 mg, 3.05 mmol), DMSO (8 mL), and 3,6-dioxabicyclo[3.1.0]hexane (260 mg, 3.0 mmol) was heated at 110° C. overnight. After cooling, the reaction mixture was diluted with EtOAc. The organic phase was washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography to afford the title compound.

후처리

  1. temperatureAfter cooling
  2. washThe organic phase was washed with aq. NaHCO3 (sat.)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-97cc728651fb49dcb451a4f899c04298
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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