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

HRID 9344

Reaction equation

HRID 9344 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c5ebe0b0aed846cc89d4466e7663f9a1
Source dataset
uspto-grants-2006_08
Patent number
US07091245B2

Linked notes

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