Cesium carbonate → 3,3,4,4-Tetrafluoro-2,3,4,5-tetrahydro-1,6-benzodioxocine-8-carbaldehyde

HRID 2264149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264149
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].FC(F)(F)S(O[CH2:17][C:18]([F:32])([F:31])[C:19]([F:30])([F:29])[CH2:20][O:21]S(C(F)(F)F)(=O)=O)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:29][C:19]1([F:30])[CH2:20][O:21][C:9]2[CH:2]=[CH:3][C:4]([CH:5]=[O:6])=[CH:7][C:8]=2[O:10][CH2:17][C:18]1([F:32])[F:31]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 943653,5-DihydroxybenzaldehydeHCID 149438532,2,3,3-Tetrafluorobutane-1,4-diyl bis(trifluoromethanesulfonate)

Produkt 1

HCID 602097233,3,4,4-Tetrafluoro-2,3,4,5-tetrahydro-1,6-benzodioxocine-8-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 2 g of 3,5-dihydroxybenzaldehyde, 10 g of 2,2,3,3-tetrafluorobutane-1,4-diyl bis(trifluoromethanesulfonate) and 12 g of cesium carbonate in 100 mL of anhydrous acetonitrile was heated under nitrogen to 50° C. overnight. The mixture was allowed to cool, then filtered and concentrated under reduced pressure. The residue was partitioned between 250 mL of ethyl acetate and 100 mL of saturated sodium carbonate then dried over magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography (0-35% ethyl acetate in hexanes) gave the product as crystalline solid. MS (m+1)=265.1; 1H NMR (400 MHz, CDCl3) 9.85 (s, 1H), 7.6 (m, 2H), 7.2 (d, 1H), 4.64 (t, 2H), 4.45 (t, 2H).

Aufarbeitung

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between 250 mL of ethyl acetate and 100 mL of saturated sodium carbonate
  5. dry with materialthen dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (0-35% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-64d15b8f533048edae3baf750ff9c5ac
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855201B2

Notizen zur Reaktion

Wird geladen…