Reacción #1869218

ord-bfba348b0a4443798a1486787f9034d3

Ecuación de reacción

O
Water
O=Cc1ccccc1O
Salicylaldehyde
O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1
(2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate
O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
O=Cc1ccccc1OC[C@@H]1CO1
subtitle compound
Rendimiento 114.8%
O=Cc1ccccc1OC[C@@H]1CO1
2-[(2S)-oxiran-2-ylmethoxy]benzaldehyde
Rendimiento 114.8%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe mixture was extracted with DCM (2×50 ml)
  2. 2
    LavadoThe combined organic extracts were washed with water (2×50 ml)
  3. 3
    OtroThe volatiles were removed in vacuo

Procedimiento

Salicylaldehyde (486 mg, 3.99 mmol) and (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (900 mg, 3.47 mmol) was dissolved in DMF (5 ml) and Cs2CO3 (1.28 g, 3.94 mmol) was added. The reaction mixture stirred for 12 at room temperature. Water (100 ml) was added, and the mixture was extracted with DCM (2×50 ml). The combined organic extracts were washed with water (2×50 ml). The volatiles were removed in vacuo to give the subtitle compound (76%, 710 mg), which was used directly in the next step.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07498338B2uspto-grants-2009_03