Hydrochloric Acid → HCID 86675234, compound

HRID 1503609Notes

Reaction equation

HRID 1503609 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([C:16]3[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=3)=[O:15])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[F:24][C:25]([Si](C)(C)C)([F:27])[F:26].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1>[N:1]1([C:6]2[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([C:16]3[CH:17]=[C:18]([Cl:23])[CH:19]=[C:20]([Cl:22])[CH:21]=3)([OH:15])[C:25]([F:27])([F:26])[F:24])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

6

Reactant 4

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

Product 1

HCID 86675234HCID 86675234, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 RT 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 RT. The reaction was extracted with DCM 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 RT
  3. extractionThe reaction was extracted with DCM
  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-6c1d83569ff54fda9570348c2d1cec58
Source dataset
uspto-grants-2015_12
Patent number
US09212163B2

Reaction notes

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