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Triphenylphosphine → Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-yl)oxy)methyl)phenyl)propanoate

HRID 1049451
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1049451
[F:1][C:2]([F:24])([F:23])[S:3]([O:6][C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[F:22])(=[O:5])=[O:4].[CH:25]1([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41]O)[CH:36]=2)[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1.O>[CH:25]1([CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][O:13][C:11]3[CH:10]=[CH:9][C:8]([C:14]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=4[F:22])=[C:7]([O:6][S:3]([C:2]([F:23])([F:1])[F:24])(=[O:5])=[O:4])[CH:12]=3)[CH:36]=2)[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:27][CH2:26]1
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Komponenten

8

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 117759876Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoateHCID 1177601232'-Fluoro-4-hydroxy-5'-methoxybiphenyl-2-yl trifluoromethanesulfonate

Produkt 1

HCID 117759787
Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-yl)oxy)methyl)phenyl)propanoate
Ausbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2′-fluoro-4-hydroxy-5′-methoxybiphenyl-2-yl trifluoromethanesulfonate (1.30 g) in THF (30 mL) were added ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (1.02 g), triphenylphosphine (1.87 g) and a 40% solution of diethyl azodicarboxylate in toluene (3.2 mL), and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.71 g) as a colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7a2e9ec96d5f4e519d635f2eeb870400
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09382188B2

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