反応 #1869206

ord-68adbf71b21c4ac5a649a3d1da610519

反応方程式

O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1
(2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate
COc1ccccc1O
2-methoxyphenol
O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
COc1ccccc1O[C@H]1CO1
subtitled compound
収率 85.3%
COc1ccccc1O[C@H]1CO1
(2S)-2-[(2-Methoxyphenoxy)]oxirane
収率 85.3%

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他The reaction mixture was partitioned between ethyl acetate and H2O
  2. 2
    乾燥The organic layer was dried over Na2SO4
  3. 3
    ろ過filtered
  4. 4
    濃縮concentrated
  5. 5
    その他The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum spirit 40-60)

実験手順

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (777 mg, 3.0 mmol), 2-methoxyphenol (372.5 mg, 3.0 mmol) and Cs2CO3 (1.3 g, 4.0 mmol) in DMF was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum spirit 40-60) to give subtitled compound (425 mg).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07498338B2uspto-grants-2009_03