4-Nitrobenzyl bromide → Diethyl 2-(4-nitrobenzyl)-2-methylmalonate

HRID 2176909ノート

反応式

HRID 2176909 の反応式
C[CH2:2][CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([O:6][CH3:7])=[O:5].[O-][CH2:14]C.[Na+].[Na].[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)([O-:20])=[O:19]>CCO>[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][C:3]([CH3:2])([C:4]([O:6][CH2:7][CH3:14])=[O:5])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:23][CH:22]=1)([O-:20])=[O:19]

参加物

6

反応物 4

HCID 660114-Nitrobenzyl bromideHCID 2723922Sodium ethoxideHCID 5088009HCID 5088009、化合物HCID 5360545Sodium

生成物 1

HCID 54496963Diethyl 2-(4-nitrobenzyl)-2-methylmalonate収率 29.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Diethyl methyl malonate (1.60 ml, 9.25 mmol) was added to a freshly prepared solution of sodium ethoxide solution [(sodium (212 mg, 9.25 mmol) in EtOH (20 ml)] and stirred for 1 h. 4-Nitrobenzyl bromide (2.00 g, 9.25 mmol) was added dropwise to the reaction mixture and stirred for 6 h at reflux. The reaction mixture was cooled to room temperature and concentrated. The residue was partitioned between water and CHCl3. The separated organic layer was washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude product. This was purified by column chromatography over silica gel (100-200 mesh) using 5% ethyl acetate in petroleum ether as eluent to afford 850 mg (29.7%) of diethyl 2-(4-nitrobenzyl)-2-methylmalonate as oily liquid.

後処理

  1. stirringstirred for 6 h
  2. temperatureat reflux
  3. concentrationconcentrated
  4. customThe residue was partitioned between water and CHCl3
  5. washThe separated organic layer was washed with water, brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude product
  10. customThis was purified by column chromatography over silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-f8188fccd9b744dba58d28e814b8cad1
出典データセット
uspto-grants-2015_06
特許番号
US09067888B2

反応ノート

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