Acetonitrile → 6-(5-Fluoro-2-methylphenyl)-1-(3-fluoro-2-nitrophenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol

HRID 400663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400663
[F:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C(#N)C.[F:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:49])=[C:34]([C:36]([CH3:48])([CH3:47])[CH2:37][C:38]([C:43]([F:46])([F:45])[F:44])([OH:42])[CH2:39][C:40]#[CH:41])[CH:35]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O1CCCC1>[F:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:49])=[C:34]([C:36]([CH3:47])([CH3:48])[CH2:37][C:38]([C:43]([F:44])([F:45])[F:46])([OH:42])[CH2:39][C:40]#[C:41][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[N+:16]([O-:18])=[O:17])[CH:35]=1

Komponenten

9

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 469390162-(1,1-Dimethyl-3-hydroxy-3-trifluoromethyl-5-hexynyl)-4-fluorotolueneHCID 600266203-Fluoro-2-nitrophenyl trifluoromethanesulphonate

Produkt 1

HCID 600264926-(5-Fluoro-2-methylphenyl)-1-(3-fluoro-2-nitrophenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-olAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 67553Tetrabutylammonium IodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of trifluoromethanesulfonic acid 3-fluoro-2-nitrophenyl ester (149 mg, 0.52 mmol), dichlorobis(triphenylphosphine)palladium (II) (20 mg, 0.028 mmol), copper (I) iodide (14 mg, 0.074 mmol), tetrabutyl ammonium iodide (200 mg, 0.54 mmol), 0.25 mL of anhydrous triethylamine, 0.5 mL of anhydrous acetonitrile, and 0.5 mL of anhydrous tetrahydrofuran was stirred at room temperature for 30 minutes. The resulting mixture was treated with 6-(5-fluoro-2-methylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (145 mg, 0.48 mmol) and stirred at room temperature for 18 hours. The crude product was purified by chromatography on SiO2 (50% hexanes in dichloromethane) to give 96 mg of the title product as light yellow oil, (45% yield).

Aufarbeitung

  1. stirringstirred at room temperature for 18 hours
  2. customThe crude product was purified by chromatography on SiO2 (50% hexanes in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-e66f46184a51474db2757ffd1848176d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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