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

HRID 2176909노트

반응식

HRID 2176909 반응식
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]

참가 물질

6

반응물 4

HCID 660114-Nitrobenzyl bromideHCID 2723922Sodium ethoxideHCID 5088009HCID 5088009, 화합물HCID 5360545Sodium

생성물 1

HCID 54496963Diethyl 2-(4-nitrobenzyl)-2-methylmalonate수율 29.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f8188fccd9b744dba58d28e814b8cad1
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067888B2

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