(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzene → 2-(4-Benzyloxy-phenyl)-ethylamine

HRID 710383

反応式

HRID 710383 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[N+:17]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][NH2:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 5702926(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzeneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 2009572-(4-Benzyloxy-phenyl)-ethylamine収率 75.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of the product of Step B (1.06 g; 4.15 mmol) in anhydrous THF (20 ml) was added drop wise to a suspension of LiAlH4 (0.52 g; 13.7 mmol) in anhydrous THF (10 ml) over a period of 1 h at room temperature with vigorous stirring. After additional stirring for 2 h, the reaction mixture was quenched with H2O (1 ml), followed by 10% NaOH (2 ml) and H2O (1 ml). This was stirred for additional 30 min and precipitate formed was filtered off, washed with CH2Cl2 (3×20 ml) and combined filtrates were evaporated to dryness to give the crude title compound (0.71 g; 75%), as a creamy foam, which was used in the next step without further purification. 1H-NMR (CDCl3) 1.5 (broad s, 2H+H2O); 2.71 (tr, 2H, J=6.8 Hz); 2.94 (tr, 2H, J=6.8 Hz); 5.04 (s, 2H); 6.17-6.84 (m, 3H); 7.17-7.43 (m, 6H).

後処理

  1. customthe reaction mixture was quenched with H2O (1 ml)
  2. stirringThis was stirred for additional 30 min
  3. customprecipitate formed
  4. filtrationwas filtered off
  5. washwashed with CH2Cl2 (3×20 ml)
  6. customwere evaporated to dryness

出典と根拠

ORDレコード
ord-bc08079d4e0a4fb9af5a744c01ebad07
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

関連ノート

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