Acetic Acid → HCID 14147965、化合物

HRID 274069ノート

反応式

HRID 274069 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]\[N+:11]([O-:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+].C(O)(=O)C.[Cl-].[Na+]>O1CCOCC1.C(O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH2:10][N+:11]([O-:13])=[O:12])[CH:4]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 1809355(Z)-1-(3-methoxyphenyl)-2-nitroetheneHCID 4311764Sodium borohydride2 回

生成物 1

HCID 14147965HCID 14147965、化合物収率 69%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
30 °C

実験手順

A solution of (Z)-1-(3-methoxyphenyl)-2-nitroethene (33.85 g) in 1,4-dioxane (315 ml) was added dropwise to an efficiently stirred suspension of sodium borohydride (15.77 g) in a mixture of 1,4-dioxane (315 ml) and ethanol (98 ml) over a period of 0.5 hour while maintaining a temperature of 30° C. After stirring for 2 hours, the resultant slurry was diluted with ice water (393 ml) and the excess sodium borohydride was decomposed with 50% aqueous acetic acid (47.4 ml). To the solution, sodium chloride (68 g) and ethyl acetate were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by distillation under reduced pressure to give 1-methoxy-3-(2-nitroethyl)benzene (23.62 g).

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. distillationThe residue was purified by distillation under reduced pressure

出典と根拠

ORDレコード
ord-06dcae5850eb40f1a79735621668f9a1
出典データセット
uspto-grants-1995_02
特許番号
US05387710

反応ノート

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