1,3-Dibromopropane → Ethyl 4-(3-bromopropoxy)mandelate

HRID 2185037

Reaktionsgleichung

Reaktionsgleichung von HRID 2185037
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.[Br:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:15][CH2:16][CH2:17][CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 111357Benzeneacetic acid, alpha,4-dihydroxy-, ethyl ester

Produkt 1

HCID 22459007Ethyl 4-(3-bromopropoxy)mandelate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of ethyl 4-hydroxymandelate (19.6 g, 0.1 mol), 1,3-dibromopropane (60.75 g, 0.3 mol) and cesium carbonate (35.75 g, 0.11 mol) in dry DMF (200 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and 1.0 N HCl. The organic layer was washed twice with water, once with brine and then dried over sodium sulfate. The organic layer was then filtered and the solvent remove in vacuo. The resulting oil was chromatographed on silica gel, using a gradient of 100% hexane to methylene chloride/hexane (2:1) to yield the titled compound.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and 1.0 N HCl
  2. washThe organic layer was washed twice with water, once with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layer was then filtered
  5. customthe solvent remove in vacuo
  6. customThe resulting oil was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-eb2ce2d22a53475989cbafb87e5ce7d8
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399640B1

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