Bromine → Ethyl 8-bromo-12-acetoxyheptadecanoate

HRID 2083278ノート

反応式

HRID 2083278 の反応式
C([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(O)=O.[Br:29]Br>C(Cl)(Cl)(Cl)Cl>[Br:29][CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

参加物

4

反応物 2

HCID 24408BromineHCID 21317594HCID 21317594、化合物

生成物 1

HCID 21317595Ethyl 8-bromo-12-acetoxyheptadecanoate

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of ethyl 8-carboxy-12-acetoxy-heptadecanoate (31.5 g., 0.079 mole), red mercuric oxide (12.8 g., 0.059 mole), and carbon tetrachloride (200 ml.) is stirred at room temperature while bromine (12.6 g., 0.079 mole) is added dropwise during one hour. The resulting mixture is heated at reflux for one hour. The mixture is then cooled, filtered, washed with dilute hydrochloric acid, water and brine and dried over sodium sulfate. The solution is evaporated in vacuo to leave the product as a yellow residual oil weighing 24.5 g. The product is purified by chromatograph on a column containing 250 g. of silica gel using chloroform as eluting solvent. There is obtained 14.4 g. of purified ethyl 8-bromo-12-acetoxyheptadecanoate, a yellow oil with Rf 0.49 on silica gel thin layer chromatograph with chloroform elution. pmr (CDCl3) δ 0.90 (3H,t); 2.03 (3H, s CH3CO); 4.07 (1H, m HCBr); 4.13 (2H, q); 4.92 (1H, m HCO).

後処理

  1. additionis added dropwise during one hour
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux for one hour
  4. temperatureThe mixture is then cooled
  5. filtrationfiltered
  6. washwashed with dilute hydrochloric acid, water and brine
  7. dry with materialdried over sodium sulfate
  8. customThe solution is evaporated in vacuo

出典と根拠

ORDレコード
ord-a5bda957c40c42af833fa282a13850a4
出典データセット
uspto-grants-1978_04
特許番号
US04085125

反応ノート

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