Stannous Chloride → 2-Benzyloxy-6-methylaniline

HRID 660828

反応式

HRID 660828 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl>CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 24479Stannous ChlorideHCID 33441871-Benzyloxy-3-methyl-2-nitrobenzene

生成物 1

HCID 27629472-Benzyloxy-6-methylaniline

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 1-benzyloxy-3-methyl-2-nitrobenzene (5.0 g, 20.6 mmol) in EtOAc (150 mL) is added SnCl2 (23.2 g, 103 mmol) and the suspension is heated at 80° C. overnight. The suspension is filtered and the filtrate washed with sat. NaHCO3 and extracted with EtOAc. The combined organic layers are washed with water, brine, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1) to give the title compound as a yellow oil.

後処理

  1. filtrationThe suspension is filtered
  2. washthe filtrate washed with sat. NaHCO3
  3. extractionextracted with EtOAc
  4. washThe combined organic layers are washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure
  8. customthe residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1)

出典と根拠

ORDレコード
ord-497302fff055418384eab6c259e66d60
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

関連ノート

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