1,3-Dibromopropane → 3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde

HRID 2264143

Reaktionsgleichung

Reaktionsgleichung von HRID 2264143
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].Br[CH2:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-:17].[Cs+].[Cs+]>C(#N)C>[O:17]1[C:9]2[CH:2]=[CH:3][C:4]([CH:5]=[O:6])=[CH:7][C:8]=2[O:10][CH2:14][CH2:13][CH2:12]1

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 943653,5-Dihydroxybenzaldehyde

Produkt 1

HCID 27763883,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 35 g of 3,5-dihydroxybenzaldehyde, 50 g (0.97 equiv) of 1,3-dibromopropane and 127 g (1.5 equiv) of cesium carbonate in 1 L of anhydrous acetonitrile was heated under nitrogen to 60° C. overnight. The mixture was allowed to cool, then filtered and concentrated under reduced pressure. The residue was partitioned between 500 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 (0-20% ethyl acetate in hexanes) gave the product as clear oil. MS (m+1)=179.1; 1H NMR (400 MHz, CDCl3) 9.82 (s, 1H), 7.42 (m, 2H), 7.02 (m, 1H), 4.32 (t, 2H), 4.24 (t, 2H), 2.22 (m, 2H).

Aufarbeitung

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between 500 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 (0-20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f4145d78c7d3416390d338d79fdb3716
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855201B2

Verknüpfte Notizen

Wird geladen…