Water → (S)-methyl 2-(6-((4'-(cyclopentyloxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280650
CS([O:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)(=O)=O.O[C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]3[CH:40]=[CH:39][C:30]4[C@H:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:32][O:33][C:29]=4[CH:28]=3)[CH:20]=2)=[C:14]([CH3:41])[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH:6]1([O:5][C:12]2[CH:13]=[C:14]([CH3:41])[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]4[CH:40]=[CH:39][C:30]5[C@H:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:32][O:33][C:29]=5[CH:28]=4)[CH:20]=3)=[C:16]([CH3:18])[CH:17]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 13066113Cyclopentyl methanesulfonateHCID 57414918(S)-methyl 2-(6-((4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

Produkt 1

HCID 73388924(S)-methyl 2-(6-((4'-(cyclopentyloxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Cyclopentyl methanesulfonate 10c (50 mg, 0.28 mmol), (S)-methyl 2-(6-((4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3 h (60 mg, 0.14 mmol), and cesium carbonate (100 mg, 0.30 mmol) were dissolved in 10 mL of N,N-dimethylformamide. The reaction mixture was heated to 80° C. and stirred for 12 hours. The resulting mixture was mixed with 10 mL of water and extracted with ethyl acetate (20 mL×2). The organic phase was washed with water (20 mL×2) and saturated sodium chloride solution (20 mL) successively, dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under the reduced pressure and the residue was purified by elution system B to obtain the title compound (S)-methyl 2-(6-((4′-(cyclopentyloxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 10d (40 mg, yield 30.0%) as a colorless slime.

Aufarbeitung

  1. extractionextracted with ethyl acetate (20 mL×2)
  2. washThe organic phase was washed with water (20 mL×2) and saturated sodium chloride solution (20 mL) successively
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under the reduced pressure
  6. customthe residue was purified by elution system B

Quellen und Nachweise

ORD-Eintrag
ord-689dee51956d4620b4e5fea72547cfd4
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139548B2

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