Sodium Thiosulfate → Methyl 2-(4-methylthiophenacyl)acetoacetate

HRID 856830ノート

反応式

HRID 856830 の反応式
CS(C1C=CC([C:9](=O)[CH2:10][CH:11]([C:16]([CH3:18])=[O:17])[C:12]([O:14][CH3:15])=[O:13])=CC=1)(=O)=O.Cl[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29](OO)=O)[CH:24]=1.[S:33]([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH3:29][C:25]1[CH:24]=[CH:23][C:28]([C:9](=[S:33])[CH2:10][CH:11]([C:16]([CH3:18])=[O:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 21862871Methyl 2-(4-methylsulfonylphenacyl)acetoacetate

生成物 1

HCID 54143420Methyl 2-(4-methylthiophenacyl)acetoacetate収率 74%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

43(ii) Methyl 2-(4-methylsulfonylphenacyl)acetoacetate 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-25ebe37eefae4f029e39fdd1e1c3b667
出典データセット
uspto-grants-2006_12
特許番号
USRE039420E1

反応ノート

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