Reacción #2358579

ord-c83b1d92c2c5446e85a18097b59b4e3b

Ecuación de reacción

C=Cc1cc(C(=O)OC)nc(-c2ccc(Oc3ccc(F)cc3)cc2)c1
methyl 6-(4-(4-fluorophenoxy)phenyl)-4-vinylpicolinate
CC(C)O.O
iPrOH H2O
COC(=O)c1cc([C@H](O)CO)cc(-c2ccc(Oc3ccc(F)cc3)cc2)n1
(S)-methyl 4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwas added AD-Mix α (1.205 g)
  2. 2
    Otrothen partitioned between 50 mL EtOAc and 25 mL water
  3. 3
    OtroThe organics were separated
  4. 4
    Secadodried over MgSO4
  5. 5
    Filtraciónfiltered
  6. 6
    Concentraciónconcentrated in vacuo

Procedimiento

To a suspension of methyl 6-(4-(4-fluorophenoxy)phenyl)-4-vinylpicolinate (0.309 g, 0.884 mmol) in 10 mL 1:1 iPrOH/H2O was added AD-Mix α (1.205 g). The reaction was stirred for 3 h then partitioned between 50 mL EtOAc and 25 mL water. The organics were separated, dried over MgSO4, filtered, and concentrated in vacuo to give crude (S)-methyl 4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)picolinate which was used in the next step without further purification (LC/MS: m/z=384.1 [M+H]+).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09120752B2uspto-grants-2015_09