1-(Trifluoroacetyl)imidazole → 1-[4-(Benzyloxy)phenyl]-4,4,4-trifluoro-2-methyl-1,3-butanedione

HRID 351229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351229
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16][CH3:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:29][C:30]([F:39])([F:38])[C:31](N1C=CN=C1)=[O:32]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:18])[CH:16]([CH3:17])[C:31](=[O:32])[C:30]([F:29])([F:38])[F:39])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 737671-(Trifluoroacetyl)imidazoleHCID 78246p-BenzyloxypropiophenoneHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 210906931-[4-(Benzyloxy)phenyl]-4,4,4-trifluoro-2-methyl-1,3-butanedione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

To a solution of 4′-benzyloxypropiophenone (6.0 g) in THF (120 ml) at −60° C. was added 38 ml of 1N lithium bis(trimethylsilyl)amide (LiHMDS), and the mixture was stirred at under −60° C. for 45 mins. 1-(Trifluoroacetyl)-imidazole (3.4 ml) was added and the mixture was stirred at −60° C. for 1 hour and at 0° C. for 30 min. The raction mixture was quenched with 0.5N HCl, the mixture was poured into EtOAc and water, and the EtOAc layer was separated, washed with brine, died over MgSO4, and concentrated to give 1-[4-(benzyloxy)phenyl]-4,4,4-trifluoro-2-methyl-1,3-butanedione.

Aufarbeitung

  1. stirringthe mixture was stirred at −60° C. for 1 hour and at 0° C. for 30 min
  2. customThe raction mixture was quenched with 0.5N HCl
  3. additionthe mixture was poured into EtOAc and water
  4. customthe EtOAc layer was separated
  5. washwashed with brine
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-037b7ae049d84577b6d7928f0a4ba1fb
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183306B2

Notizen zur Reaktion

Wird geladen…