tert-Butyl hydroperoxide → 3-Chloromethylsulfonyl-2,5-dihydrofuran

HRID 2397646ノート

反応式

HRID 2397646 の反応式
ClCS(Br)(=O)=O.O1CC=CC1.C(OO)(C)(C)C.[Cl:18][CH2:19][S:20]([CH:23]1[CH:27](Br)[CH2:26][O:25][CH2:24]1)(=[O:22])=[O:21]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:18][CH2:19][S:20]([C:23]1[CH2:24][O:25][CH2:26][CH:27]=1)(=[O:22])=[O:21]

参加物

7

反応物 4

HCID 6410tert-Butyl hydroperoxideHCID 155702,5-DihydrofuranHCID 12543458Chloromethanesulfonyl bromideHCID 125434603-Chloromethylsulfonyl-4-bromotetrahydrofuran

生成物 1

HCID 125434643-Chloromethylsulfonyl-2,5-dihydrofuran

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒2 回HCID 8471Triethylamine溶媒

反応条件

温度
20 °C

実験手順

19.3 g (0.1 mole) of chloromethanesulfonic acid bromide are added in the course of 10 minutes to a solution of 14 g (0.2 mole) of 2,5-dihydrofuran and 0.5 ml of tert.-butyl hydroperoxide in 30 ml of chloroform at -40° C. After 15 minutes, 16.5 ml of triethylamine, dissolved in 20 ml of chloroform, are added dropwise at the same temperature, so as to dehydrobrominate the 3-chloromethylsulfonyl-4-bromotetrahydrofuran which has been formed. The mixture is stirred for half an hour at 20° C., washed with water, dried and concentrated. The residue is repeatedly digested with ether and the ether extract is distilled; it boils at 115°-120° C./0.2 mm Hg. 4.8 g of 3-chloromethylsulfonyl-2,5-dihydrofuran are obtained.

後処理

  1. additionare added dropwise at the same temperature
  2. customhas been formed
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. extractionthe ether extract
  7. distillationis distilled

出典と根拠

ORDレコード
ord-c69709345a124c82a16b49248c049f35
出典データセット
uspto-grants-1977_05
特許番号
US04022804

反応ノート

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