Water → HCID 17934659, Verbindung

HRID 489227

Reaktionsgleichung

Reaktionsgleichung von HRID 489227
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=1.O>C(Cl)Cl>[C:24]([O:23][C:21](=[O:22])[C:20]1[CH:28]=[CH:29][C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:18][CH:19]=1)([CH3:27])([CH3:25])[CH3:26]

Komponenten

5

Edukt 3

HCID 962WaterHCID 67749Trifluoromethanesulfonic anhydrideHCID 117640tert-Butyl 4-hydroxybenzoate

Produkt 1

HCID 17934659HCID 17934659, VerbindungAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (1.04 ml, 6.2 mmol) was added to a cooled (5° C.) solution of tert-butyl 4-hydroxybenzoate (1 g, 5.1 mmol) in a mixture of DCM (25 ml) and TEA (1.1 ml, 7.8 mmol). After 4 h at 5° C., water was added. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed over silica gel (eluent: cyclohexane/iPr2O 95/5) to yield the above-titled compound as a colorless oil (1.45 g). 1H NMR (CDCl3): 8.09 (2H, d, J=8.6 Hz), 7.32 (2H, d, J=8.6 Hz), 1.60 (9H, s).

Aufarbeitung

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed over silica gel (eluent: cyclohexane/iPr2O 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-ba8d1a6d6ea141dfb286a494f23b81fe
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977267B2

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