2-t-Butyl-5-[(1E)-3-(t-butyldimethylsilyloxy)propenyl]-1-nitrobenzene → 2-t-Butyl-5-(3-t-butyldimethylsilyloxypropyl)aniline

HRID 1418184ノート

反応式

HRID 1418184 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:7][C:6]=1[N+:22]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)C.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])=[CH:7][C:6]=1[NH2:22])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 193487852-t-Butyl-5-[(1E)-3-(t-butyldimethylsilyloxy)propenyl]-1-nitrobenzeneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 193485532-t-Butyl-5-(3-t-butyldimethylsilyloxypropyl)aniline収率 84.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 3283Diethyl Ether溶媒

実験手順

A solution of 16.0 g of 2-t-butyl-5-[(1E)-3-(t-butyldimethylsilyloxy)-propenyl]-1-nitrobenzene [prepared as described in step (iv) above] in 800 ml of diethyl ether was stirred at room temperature for 3 hours in the presence of 8.0 g of 10% palladium-on-charcoal under a stream of hydrogen. At the end of this time, the reaction mixture was filtered and the filtrate was freed from the solvent by distillation under reduced pressure . The residue was purified by column chromatography through silica gel, using a 1:10 by volume mixture of ethyl acetate and hexane as the eluent, to give 12.5 g of the title compound as an oily substance.

後処理

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. distillationthe filtrate was freed from the solvent by distillation under reduced pressure
  3. customThe residue was purified by column chromatography through silica gel
  4. additionby volume mixture of ethyl acetate and hexane as the eluent

出典と根拠

ORDレコード
ord-f77860948e7848a2a5869d1a25f1b731
出典データセット
uspto-grants-1999_03
特許番号
US05880147

反応ノート

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