Triphenylphosphine → {4-[3,3-Bis-(4-pyridin-3-yl-phenyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester

HRID 9344

Reaktionsgleichung

Reaktionsgleichung von HRID 9344
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.[N:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]2[CH:49]=[CH:48][C:47]([C:50]([C:54]3[CH:59]=[CH:58][C:57]([C:60]4[CH:61]=[N:62][CH:63]=[CH:64][CH:65]=4)=[CH:56][CH:55]=3)=[CH:51][CH2:52]O)=[CH:46][CH:45]=2)[CH:39]=1.[CH2:66]([O:68][C:69](=[O:83])[CH2:70][O:71][C:72]1[CH:77]=[CH:76][C:75]([SH:78])=[CH:74][C:73]=1[C:79]([F:82])([F:81])[F:80])[CH3:67]>C1COCC1>[CH2:66]([O:68][C:69](=[O:83])[CH2:70][O:71][C:72]1[CH:77]=[CH:76][C:75]([S:78][CH2:52][CH:51]=[C:50]([C:54]2[CH:59]=[CH:58][C:57]([C:60]3[CH:61]=[N:62][CH:63]=[CH:64][CH:65]=3)=[CH:56][CH:55]=2)[C:47]2[CH:46]=[CH:45][C:44]([C:40]3[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=3)=[CH:49][CH:48]=2)=[CH:74][C:73]=1[C:79]([F:80])([F:81])[F:82])[CH3:67]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 219868193,3-Bis-(4-pyridin-3-yl-phenyl)-prop-2-en-1-olHCID 59516001Ethyl [4-sulfanyl-2-(trifluoromethyl)phenoxy]acetate

Produkt 1

HCID 69620630{4-[3,3-Bis-(4-pyridin-3-yl-phenyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triphenylphosphine (138 mg, 0.68 mmol) and ADDP (173 mg, 0.68 mmol) were added to a solution of 3,3-bis-(4-pyridin-3-yl-phenyl)-prop-2-en-1-ol (100 mg, 0.27 mmol) in THF (5 ml) at 0° C. The reaction mixture was stirred for 5 min under nitrogen atmosphere. (4-Mercapto-2-trifluoromethyl-phenoxy)-acetic acid ethyl ester (prepared analogous to procedure in BioOrg. Med. Chem. Lett. 2003, 13, 1517) (92 mg, 0.32 mmol) was slowly added to the reaction mixture and the reaction was stirred for further 2 h at 0° C. The reaction mixture was evaporated and the residue was triturated with ether (2×15 ml). The filtered ether phases were evaporated and purified by column chromatography (eluent: ethyl acetate) to give {4-[3,3-bis-(4-pyridin-3-yl-phenyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester in 100 mg (60%) yield.

Aufarbeitung

  1. stirringthe reaction was stirred for further 2 h at 0° C
  2. customThe reaction mixture was evaporated
  3. customthe residue was triturated with ether (2×15 ml)
  4. customThe filtered ether phases were evaporated
  5. custompurified by column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c5ebe0b0aed846cc89d4466e7663f9a1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091245B2

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