Dichloromethane → 2-Benzyl-4-ethoxy-6-allyl-7-hydroxysaccharin

HRID 266474

反応式

HRID 266474 の反応式
[CH2:1]([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([O:23]CC=C)[CH:14]=[CH:15][C:16]=2[O:20][CH2:21][CH3:22])[S:9]1(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCOCCO[CH2:35][CH2:36]OC.Cl[CH2:40]Cl>>[CH2:1]([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([OH:23])[C:14]([CH2:40][CH:35]=[CH2:36])=[CH:15][C:16]=2[O:20][CH2:21][CH3:22])[S:9]1(=[O:10])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 8189TriglymeHCID 700509212-Benzyl-4-ethoxy-7-allyloxysaccharin

生成物 1

HCID 700530822-Benzyl-4-ethoxy-6-allyl-7-hydroxysaccharin収率 36%

反応条件

温度
200 °C

実験手順

A mixture of 2-benzyl-4-ethoxy-7-allyloxysaccharin (0.25 g) and triglyme was heated at 200° C. for 20 minutes, examined for extent of reaction by thin layer chromatography, heated at 200° C. for 20 minutes more, stirred overnight and poured into ice-water. The resulting tacky, brown solid was dissolved in dichloromethane. The dichloromethane solution was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and stripped of dichloromethane. Column chromatography of the residue (0.29 g) on silica using dichloromethane and dichloromethane-acetone (up to 99:1) as eluants afforded 2-benzyl-4-ethoxy-6-allyl-7-hydroxysaccharin (90 mg, 36% yield) whose mass spectrogram showed a molecular ion at mass 373.

後処理

  1. customexamined for extent of reaction by thin layer chromatography
  2. temperatureheated at 200° C. for 20 minutes more
  3. washThe dichloromethane solution was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-7fd7ed211adf49958b19d8715b7eccaf
出典データセット
uspto-grants-1997_07
特許番号
US05650422

関連ノート

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