N-Allyl-2,2,2-trifluoroacetamide → (E)-N-(3-(3-(cycloheptylmethoxy)phenyl)allyl)-2,2,2-trifluoroacetamide

HRID 875502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875502
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:17]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:18]=[CH2:19]>>[CH:7]1([CH2:6][O:5][C:4]2[CH:3]=[C:2](/[CH:19]=[CH:18]/[CH2:17][NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:16]=[CH:15][CH:14]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

3

Edukt 2

HCID 558569N-Allyl-2,2,2-trifluoroacetamideHCID 67317652((3-Bromophenoxy)methyl)cycloheptane

Produkt 1

HCID 86637611(E)-N-(3-(3-(cycloheptylmethoxy)phenyl)allyl)-2,2,2-trifluoroacetamide

Versuchsvorschrift

((3-Bromophenoxy)methyl)cycloheptane was coupled with N-allyl-2,2,2-trifluoroacetamide following the method used in Example 10 except that the mixture was heated for 23 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and partitioned between EtOAc and water. The combined organics were washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (10% EtOAc-hexanes) gave (E)-N-(3-(3-(cycloheptylmethoxy)phenyl)allyl)-2,2,2-trifluoroacetamide. Yield (0.7015 g, 52%): 1H NMR (400 MHz, CDCl3) δ 7.23 (t, J=7.6 Hz, 1H), 6.90-6.94 (m, 2H), 6.81 (dd, J=8.4, 1.6 Hz, 1H), 6.56 (d, J=15.6 Hz, 1H), 6.39 (br s, 1H), 6.12-6.19 (m, 1H), 4.13 (t, J=6.0 Hz, 2H), 3.73 (d, J=9.6 Hz, 2H), 1.92-2.10 (m, 1H), 1.82-1.90 (m, 2H), 1.42-1.76 (m, 8H), 1.24-1.36 (m, 2H).

Aufarbeitung

  1. temperaturewas heated for 23 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between EtOAc and water
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (10% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-195bfd5150ae440db0ad9272d159b61e
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981153B2

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