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2-(Trifluoromethyl)oxirane → 3-[[[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]methyl]-(3,3,3-trifluoro-2-hydroxypropyl)amino]benzonitrile

HRID 1016996
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1016996
[F:1][C:2]([F:23])([O:6][C:7]1[CH:8]=[C:9]([CH2:13][NH:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].[F:24][C:25]([F:30])([F:29])[CH:26]1[O:28][CH2:27]1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C>[F:1][C:2]([F:23])([O:6][C:7]1[CH:8]=[C:9]([CH2:13][N:14]([CH2:27][CH:26]([OH:28])[C:25]([F:30])([F:29])[F:24])[C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:4])[F:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 5207692-(Trifluoromethyl)oxiraneHCID 2733225Ytterbium triflateHCID 235060273-[[[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]methyl]amino]benzonitrile

Produkt 1

HCID 235060423-[[[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]methyl]-(3,3,3-trifluoro-2-hydroxypropyl)amino]benzonitrileAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The benzonitrile (1.58 g, 4.88 mmol) from EX-576A and 1,1,1-trifluoro-2,3-epoxy-propane (546 mL, 6.34 mmol) were dissolved in 4 mL of acetonitrile. Ytterbium (III) trifluoromethanesulfonate (304 mg, 0.49 mmol) was added, and the stirred solution was warmed to 50° C. overnight. The reaction was quenched with water and extracted with ether. The ether layer was washed with brine, dried over MgSO4 and evaporated. The crude product was purified by MPLC on silica gel eluting with dichloromethane to give 1.61 g (76%) of the desired 3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]-(3,3,3-trifluoro-2-hydroxypropyl)amino]benzonitrile product as a clear oil, greater than 98% by reverse phase HPLC. HRMS calcd. for C19H15F7N2O2: 437.1100 [M+H]+, found: 437.1097. 1H NMR (CDCl3) δ3.60-3.69 (m, 1H), 3.86 (d, 1H), 4.32 (bs. 1H), 4.69 (q, 2H), 5.86 (dt, 1H), 6.85-6.95 (m, 2H), 6.97-7.01 (m, 2H), 7.04-7.12 (m, 2H), 7.23-7.37 (m, 2H).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with ether
  3. washThe ether layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product was purified by MPLC on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-4ed34e93f9224afcafe491158f3ed54c
Quelldatensatz
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06476057B1

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