Hydrochloric Acid → HCID 86675235, compound

HRID 587767Notes

Reaction equation

HRID 587767 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([OH:19])[C:15]([F:18])([F:17])[F:16])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.N1(C2C=CC(/C=C/C(C3C=C(Cl)C=C(Cl)C=3)=O)=CC=2)C=N[CH:30]=N1.FC([Si](C)(C)C)(F)F.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1>[Cl:27][C:22]1[CH:21]=[C:20]([C:14]([O:19][CH3:30])([C:15]([F:18])([F:17])[F:16])/[CH:13]=[CH:12]/[C:9]2[CH:10]=[CH:11][C:6]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[CH:7][CH:8]=2)[CH:25]=[C:24]([Cl:26])[CH:23]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 86675233HCID 86675233, compoundHCID 86675234HCID 86675234, compound

Product 1

HCID 86675235HCID 86675235, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-4-(4-(1H-1,2,4-triazol-1-yl)phenyl)-2-(3,5-dichlorophenyl)-1,1,1-trifluorobut-3-en-2-ol (DC69): To a solution of (E)-3-(4-(1H-1,2,4-triazol-1-yl)phenyl)-1-(3,5-dichlorophenyl)prop-2-en-1-one (1 g, 3 mmol) in THF (150 mL) was added trifluoromethyltrimethylsilane (0.517 g, 3.644 mmol) and tetra-n-butylammonium fluoride (TBAF) (1.0 M, 1 mL) at 0° C. The reaction was slowly warmed to ambient temperature and allowed to stir for 2 h. The reaction was then cooled to 0° C. and 5 M HCl solution was added and the reaction was stirred for an additional 4 h at ambient temperature. The reaction was extracted with CH2Cl2 and the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude compound was purified by flash column chromatography (SiO2; 25% EtOAc/hexanes) to afford the title compound as an off-white solid (0.3 g, 25%).

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. stirringthe reaction was stirred for an additional 4 h at ambient temperature
  3. extractionThe reaction was extracted with CH2Cl2
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude compound was purified by flash column chromatography (SiO2; 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d2fbf32897eb4631b03530c13ef287e1
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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