Triethylamine → 2-(2,6-Dinitrophenyl)ethoxycarbonyl chloride

HRID 963750ノート

反応式

HRID 963750 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][CH2:14][OH:15])([O-:3])=[O:2].CCN(CC)CC.[Cl:23][C:24](OC(Cl)(Cl)Cl)=[O:25]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][CH2:14][O:15][C:24]([Cl:23])=[O:25])([O-:3])=[O:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 108675832-(2,6-Dinitrophenyl)ethanol

生成物 1

HCID 190827052-(2,6-Dinitrophenyl)ethoxycarbonyl chloride収率 97.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 2-(2,6-dinitrophenyl)ethanol (4.08 g, 19.23 mmol) and Et3N (2.7 ml, 19.28 mmol) in THF (30 ml, dist. over CaH2) was dropped in a solution, cooled to 0° C., of trichloromethyl chloroformate (3.81 g, 2.33 ml, 19.28 mmol) in THF (10 ml, see above) for 20 min. This solution was stirred for 25 min while cooling in an ice bath, and was then stirred for 1 h 45 min at room temperature. The mixture was filtered over Celite. Rewashing the filter cake with THF, removing the solvent and excess reagent from the pooled filtrates by distillation and drying in a high vacuum yielded 5.13 g 2-(2,6-dinitrophenyl)-ethoxycarbonyl chloride (97%) as a light-brown solid.

後処理

  1. temperaturewhile cooling in an ice bath
  2. stirringwas then stirred for 1 h 45 min at room temperature
  3. filtrationThe mixture was filtered over Celite
  4. customremoving the solvent and excess reagent from the pooled filtrates
  5. distillationby distillation
  6. customdrying in a high vacuum

出典と根拠

ORDレコード
ord-791c3164c9eb486b8a01e2622374f8fc
出典データセット
uspto-grants-1998_06
特許番号
US05763599

反応ノート

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