1-Chloro-3-(2-nitroethenyl)benzene → 1-Chloro-3-(2-nitroethyl)benzene

HRID 6394

反応式

HRID 6394 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N+:10]([O-:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>O1CCOCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N+:10]([O-:12])=[O:11])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 27316461-Chloro-3-(2-nitroethenyl)benzeneHCID 4311764Sodium borohydride

生成物 1

HCID 197933101-Chloro-3-(2-nitroethyl)benzene収率 48%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

A solution of 13.5 g (72 mmol) of 2-(3-Chlorophenyl)-1-nitroethene, from Step 2, in 200 mL of dioxane was added dropwise to a stirred suspension of 6 g (157 mmol) of sodium borohydride in a mixture of 140 mL of dioxane and 60 mL of ethanol. The reaction mixture was stirred at ambient temperature for 2 h and then the excess borohydride was quenched with acid. The reaction mixture was concentrated in vacuo and the residue was partitioned between methylene chloride and water (4:1). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silica gel eluted with 20% methylene chloride in hexane to afford 6.3 g (48% yield) of the title compound; MS DCl--NH3M/Z: 203 (M+NH4)+ ; 1H NMR (CDCl3) δ3.3 (2H, t, J=7.5 Hz), 4.6 (2H, t, J= 7.5 Hz), 7.05-7.3 (4H, m).

後処理

  1. customthe excess borohydride was quenched with acid
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between methylene chloride and water (4:1)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified on silica gel
  8. washeluted with 20% methylene chloride in hexane

出典と根拠

ORDレコード
ord-8ba885339f8d41249dc7afe4b839d218
出典データセット
uspto-grants-1993_09
特許番号
US05248677

関連ノート

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