Trifluoroacetic anhydride → HCID 68864572, Verbindung

HRID 1726000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1726000
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:13]([C:25]([O:27][CH3:28])=[O:26])=[C:14]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)[CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:9].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[O-]S(C(F)(F)F)(=O)=O.[Ga+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>ClC(Cl)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:13]([C:25]([O:27][CH3:28])=[O:26])=[C:14]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[C:15]2=[CH:16][CH:17]=1)(=[O:9])=[O:10]

Komponenten

5

Edukt 3

HCID 9845Trifluoroacetic anhydrideHCID 2733940GALLIUM(III) TRIFLUOROMETHANESULFONATEHCID 68866177HCID 68866177, Verbindung

Produkt 1

HCID 68864572HCID 68864572, VerbindungAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of Example 510E (3.74 g, 9.13 mmol) in dichloroethane (183 mL) was treated with trifluoroacetic anhydride (2.58 mL, 18.3 mmol) and gallium (III) triflate (0.944 g, 1.83 mmol), stirred at 90° C. for 1.5 hours, and cooled to room temperature. The reaction was quenched with saturated aqueous sodium bicarbonate (200 mL), and the aqueous layer was extracted with CH2Cl2 (4×50 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography (7:3 hexanes/ethyl acetate) to provide the desired product (2.73 g, 76%). MS (ESI(+)) m/e 392 (M+H)+, 409 (M+NH4)+, 414 (M+Na)+; MS (ESI(−)) m/e 390 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.46 (br s, 1H), 7.74 (m, 2H), 7.52 (d, 1H), 7.43 (dd, 1H), 7.35 (td, 1H), 7.25 (d, 1H), 3.70 (s, 3H), 2.67 (t, 2H), 2.61 (m, 2H), 1.72 (m, 2H), 1.60 (m, 2H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate (200 mL)
  3. extractionthe aqueous layer was extracted with CH2Cl2 (4×50 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash chromatography (7:3 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7b8b18f9400b4abe850cd9c8c69f045d
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491718B2

Notizen zur Reaktion

Wird geladen…