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

HRID 710383

반응식

HRID 710383 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 2009572-(4-Benzyloxy-phenyl)-ethylamine수율 75.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bc08079d4e0a4fb9af5a744c01ebad07
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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