Dichloromethane → Methyl 2-(4-methylsulfonylphenacyl)acetoacetate

HRID 1415761ノート

反応式

HRID 1415761 の反応式
CC1C=CC(C(=S)[CH2:7][CH:8]([C:13]([CH3:15])=[O:14])[C:9]([O:11][CH3:12])=[O:10])=CC=1.Cl[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([O:28]O)=O)[CH:21]=1.[S:30]([O-:34])([O-])(=[O:32])=S.[Na+].[Na+].[CH2:37](Cl)Cl>>[CH3:37][S:30]([C:25]1[CH:20]=[CH:21][C:22]([C:26](=[O:28])[CH2:7][CH:8]([C:13]([CH3:15])=[O:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:23][CH:24]=1)(=[O:34])=[O:32]

参加物

5

反応物 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 54143420Methyl 2-(4-methylthiophenacyl)acetoacetate

生成物 1

HCID 21862871Methyl 2-(4-methylsulfonylphenacyl)acetoacetate収率 74%

実験手順

4.42 g (15.8 mmol) of methyl 2-(4-methylthiophenacyl)acetoacetate [prepared as described in step (i) above] were dissolved in 150 ml of methylene chloride, and 7.77 g (31.5 mmol) of 70% m-chloroperbenzoic acid were added to the resulting solution, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour. 30 ml of a 10% w/v aqueous solution of sodium thiosulfate were added to the mixture, and the mixture was vigorously shaken, after which it separated into liquid phases. The organic layer was separated and washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate and the solvent was then removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 1:1 by volume mixture of ethyl acetate and hexane, to give 3.65 g (yield 74%) of the title compound as a slightly yellow powder.

後処理

  1. temperaturecooling
  2. stirringthe mixture was vigorously shaken
  3. customafter which it separated into liquid phases
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialafter which it was dried over anhydrous magnesium sulfate
  7. customthe solvent was then removed by distillation under reduced pressure
  8. washeluted with a 1:1 by volume mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-b2ca143798c946a0a97a4db9d2f939f7
出典データセット
uspto-grants-1999_06
特許番号
US05908858

反応ノート

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