Reaktion #417925

ord-b8ad28415376456983e7b827940bb22f

Reaktionsgleichung

COC(=O)c1ccc(O)cc1
32
COC(=O)c1ccc(O)cc1
methyl 4-hydroxybenzoate
O=C([O-])[O-].[K+].[K+]
K2CO3
CCCCCC/C=C\CCCI
13
CCCCCC/C=C\CCCI
1-iodoundec-4Z-ene
CCCCCC/C=C\CCCOc1ccc(C(=O)OC)cc1
yellow oil
Ausbeute 100.1%
CCCCCC/C=C\CCCOc1ccc(C(=O)OC)cc1
methyl 4-(undec-4Z-enyloxy)benzoate
Ausbeute 100.1%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter reaction for 7 hours at 90° C.
  2. 2
    Einengenthe reaction medium is concentrated
  3. 3
    Waschenwashed with water

Vorschrift

90 mg of 32 (590 μmol) and 81 mg of K2CO3 (590 μmol) are added to 150 mg of 13 (535 μmol) in anhydrous DMF (2 mL). After reaction for 7 hours at 90° C., the reaction medium is concentrated, taken up in DCM and then washed with water. 163 mg of a yellow oil are obtained, and are chromatographed on silica gel in pentane/ethyl acetate (80/1). 129 mg of the expected coupling product are isolated in the form of a yellow oil, i.e. a yield of 79%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08877684B2uspto-grants-2014_11