Sodium hydride → t-Butyl 3-nitrobenzyloxyacetate

HRID 260315

반응식

HRID 260315 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 22401159t-Butyl 3-nitrobenzyloxyacetate수율 88%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-acea8aa7dfb041c3bd43bcaaea3b9530
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527791

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