Sodium hydride → 1-(4-Tert-butyldimethylsilyloxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinone

HRID 274939ノート

反応式

HRID 274939 の反応式
[C:1]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15])([O:3][CH2:4][CH3:5])=[O:2].[H-].[Na+].[Si:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][C:27]=1[CH2:34][CH2:35][CH3:36])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[C:7]2=[O:15])=[CH:28][C:27]=1[CH2:34][CH2:35][CH3:36])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylateHCID 200892104-Tert-butyldimethylsilyloxy-3-propylbenzyl bromide

生成物 1

HCID 200891961-(4-Tert-butyldimethylsilyloxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinone収率 64%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 0.295 g (1.43 mmol) of 1-carboethoxy-2-benzimidazolinone dissolved in 5.0 mL DMF was added 0.063 g (1.57 mmol) of a 60% oil dispersion of sodium hydride and the resulting mixture was stirred under a nitrogen atmosphere and gently warmed with a heat gun until the solids had dissolved and gas evolution had ceased. A solution of the product of step A in 2.0 mL DMF was then added and the reaction mixture was stirred for an additional 0.5 hours. The mixture was then quenched with 10% aqueous citric acid and extracted into ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate and brine, dried (MgSO4), filtered and evaporated, and then the residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.088 g (64%) of the title compound.

後処理

  1. temperaturegently warmed with a heat gun until the solids
  2. dissolutionhad dissolved
  3. stirringthe reaction mixture was stirred for an additional 0.5 hours
  4. customThe mixture was then quenched with 10% aqueous citric acid
  5. extractionextracted into ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with saturated sodium bicarbonate and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customthe residue was purified on a silica gel flash chromatography column
  12. washeluted with 30% EtOAc-hexane
  13. customEvaporation of the purified fractions
  14. customdrying in vacuo

出典と根拠

ORDレコード
ord-842cb5f8ca674bc9866193082f4058b7
出典データセット
uspto-grants-1995_02
特許番号
US05391566

反応ノート

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