Triethylamine → HCID 20354852、化合物

HRID 442431ノート

反応式

HRID 442431 の反応式
C([O:4][C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[CH2:10][CH2:11][CH:12]([O:18][C:19](=[O:21])[CH3:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=O)C.BrBr.C(N(CC)CC)C>C(Cl)(Cl)(Cl)Cl>[C:19]([O:18][CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10][C:6]1[C:5](=[O:4])[CH2:9][CH2:8][CH:7]=1)(=[O:21])[CH3:20]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24408BromineHCID 20354840HCID 20354840、化合物

生成物 1

HCID 20354852HCID 20354852、化合物収率 56.9%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒2 回

実験手順

To a stirred solution of 1-acetoxy-2-(3-acetoxyoctyl)cyclopent-1-ene (59.2 g.) [prepared as described in (e) above] in dry carbon tetrachloride (350 ml.) was added dropwise, during 30 minutes, a solution of bromine (32 g.) in dry carbon tetrachloride (100 ml.) at -10° to -5° C. The solution was stirred for a further 20 minutes without cooling. Triethylamine (22.2 g.) was then added and the resulting mixture stirred and refluxed for 90 minutes. The mixture was filtered, and the filtrate washed with aqueous 2N sodium carbonate and with water. After drying over magnesium sulphate and evaporation of the solvent in vacuo, the residue was distilled, in the presence of a few crystals of potassium acetate, at 132°-168° C./0.25 mm.Hg, to give crude 2-(3-acetoxyoctyl)cyclopent-2-enone. This was redistilled, with potassium acetate, at 116°- 135° C./0.15 mm.Hg to give 2-(3-acetoxyoctyl)cyclopent-2-enone (28.7 g.), nD28 = 1.470.

後処理

  1. customat -10° to -5° C
  2. temperaturewithout cooling
  3. stirringthe resulting mixture stirred
  4. temperaturerefluxed for 90 minutes
  5. filtrationThe mixture was filtered
  6. washthe filtrate washed with aqueous 2N sodium carbonate and with water
  7. dry with materialAfter drying over magnesium sulphate and evaporation of the solvent in vacuo
  8. distillationthe residue was distilled, in the presence of a few crystals of potassium acetate, at 132°-168° C./0.25 mm.Hg
  9. customto give crude 2-(3-acetoxyoctyl)cyclopent-2-enone
  10. distillationThis was redistilled, with potassium acetate, at 116°- 135° C./0.15 mm.Hg

出典と根拠

ORDレコード
ord-1931b0300ca142cd94ecd29b6c19d967
出典データセット
uspto-grants-1977_08
特許番号
US04045467

反応ノート

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