Réaction #417923

ord-a5000d5875934389b6e4667f7438b2d9

Équation de réaction

COC(=O)c1ccccc1O
28
COC(=O)c1ccccc1O
methyl 2-hydroxybenzoate
O=C([O-])[O-].[K+].[K+]
K2CO3
CCCCCC/C=C\CCCI
13
CCCCCC/C=C\CCCI
1-iodoundec-4Z-ene
CCCCCC/C=C\CCCOc1ccccc1C(=O)OC
yellow oil
Rendement 90.0%
CCCCCC/C=C\CCCOc1ccccc1C(=O)OC
methyl 2-(undec-4Z-enyloxy)benzoate
Rendement 90.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreAfter reaction for 8 hours at 90° C.
  2. 2
    Concentrationthe reaction medium is concentrated
  3. 3
    Lavagewashed with water

Mode opératoire

88 mg of 28 (578 μmol) and 77 mg of K2CO3 (557 mmol) are added to 140 mg of 13 (500 μmol) in anhydrous DMF (2 mL). After reaction for 8 hours at 90° C., the reaction medium is concentrated, taken up in DCM and then washed with water. 137 mg of a yellow oil are obtained, and are chromatographed on silica gel in pentane/ethyl acetate (40/1). 100 mg of a yellow oil are isolated, i.e. a yield of 66%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08877684B2uspto-grants-2014_11