Dimethyl Sulfide → 2-Methyl-4-oxo-4H-chromene-8-carbaldehyde

HRID 1947231ノート

反応式

HRID 1947231 の反応式
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2/[CH:13]=C/C.[O:16]=[O+][O-].CSC>ClCCl>[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[O:16]

参加物

5

反応物 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 574388872-Methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one

生成物 1

HCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-60 °C

実験手順

18.5 g (62.8 mmol) of 2-methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one are dissolved in 400 ml of dichloromethane and cooled to −60° C. Ozone is passed into the reaction solution for 30 min. Dimethyl sulfide is then added to the reaction mixture. After warming to room temperature, the solvent is removed in vacuo and the residue is slurried in a little methanol. The solid remaining after filtration is recrystallized from diethyl ether. 9.1 g (77.4% of theory) of the title compound are obtained.

後処理

  1. temperatureAfter warming to room temperature
  2. customthe solvent is removed in vacuo
  3. filtrationafter filtration
  4. customis recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-07043bdf6d7d4de090bc73e137487ec1
出典データセット
uspto-grants-2013_03
特許番号
US08399471B2

反応ノート

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