Sodium hydride → t-Butyl 3-nitrobenzyloxyacetate

HRID 260315

反応式

HRID 260315 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][OH:8])([O-:3])=[O:2].[H-].[Na+].Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][O:8][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([O-:3])=[O:2]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 692673-Nitrobenzyl alcoholHCID 79177tert-Butyl bromoacetate

生成物 1

HCID 22401159t-Butyl 3-nitrobenzyloxyacetate収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Nitrobenzyl alcohol (5 g, 32.6 mM) was dissolved in DMF (200 ml) and cooled to 5°. Sodium hydride (60% in oil, 1.57 g, 39.2 mM) was added to the stirred solution in portions over 30 minutes, and the mixture cooled to -20°. t-Butyl bromoacetate (5.27 ml, 32.6 mM) was run in dropwise, and the mixture allowed to warm to ambient temperature overnight. Solvent was evaporated, the residue treated with water, and organics extracted into ethyl acetate. The combined organic layers were washed with water and brine, and dried over MgSO4. Crude product was purified by chromatography on silica, eluting with a gradient from hexane/dichloromethane (95:5) to dichloromethane, to give t-butyl 3-nitrobenzyloxyacetate (7.71 g, 88%).

後処理

  1. temperaturecooled to 5°
  2. temperaturethe mixture cooled to -20°
  3. customSolvent was evaporated
  4. additionthe residue treated with water
  5. extractionorganics extracted into ethyl acetate
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over MgSO4
  8. customCrude product was purified by chromatography on silica
  9. washeluting with a gradient from hexane/dichloromethane (95:5) to dichloromethane

出典と根拠

ORDレコード
ord-acea8aa7dfb041c3bd43bcaaea3b9530
出典データセット
uspto-grants-1996_06
特許番号
US05527791

関連ノート

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