反応 #1869218

ord-bfba348b0a4443798a1486787f9034d3

反応方程式

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
収率 114.8%
O=Cc1ccccc1OC[C@@H]1CO1
2-[(2S)-oxiran-2-ylmethoxy]benzaldehyde
収率 114.8%

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    抽出the mixture was extracted with DCM (2×50 ml)
  2. 2
    洗浄The combined organic extracts were washed with water (2×50 ml)
  3. 3
    その他The volatiles were removed in vacuo

実験手順

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.

出典

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