Water → Methyl 2-methyl-2-(4-methylsulfonylphenacyl)acetoacetate

HRID 1415764ノート

反応式

HRID 1415764 の反応式
[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([C:9](=[O:19])[CH2:10][CH:11]([C:16]([CH3:18])=[O:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].[CH3:24]I.O>O1CCCC1>[CH3:24][C:11]([CH2:10][C:9]([C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:21][CH:20]=1)=[O:19])([C:16]([CH3:18])=[O:17])[C:12]([O:14][CH3:15])=[O:13]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21862871Methyl 2-(4-methylsulfonylphenacyl)acetoacetate

生成物 1

HCID 21862826Methyl 2-methyl-2-(4-methylsulfonylphenacyl)acetoacetate収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.65 g (2.1 mmol) of methyl 2-(4-methylsulfonylphenacyl)acetoacetate [prepared as described in Example 43(ii)] was dissolved in 20 ml of anhydrous tetrahydrofuran, and 92 mg (2.3 mmol) of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to the resulting solution, whilst ice-cooling and under a nitrogen atmosphere. The mixture was stirred for 10 minutes, after which 1.1 ml (2.5 mmol) of methyl iodide were added, whilst ice-cooling, and the mixture was stirred for 2 hours. At the end of this time, water was added to the mixture, which was then extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 2:3 by volume mixture of ethyl acetate and hexane, to give 0.54 g (yield 80%) of the title compound as a slightly yellow powder.

後処理

  1. temperaturecooling and under a nitrogen atmosphere
  2. temperaturecooling
  3. stirringthe mixture was stirred for 2 hours
  4. extractionwas then extracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with a saturated aqueous solution of sodium chloride
  7. dry with materialafter which it was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. washeluted with a 2:3 by volume mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-23a6da484a3041169afc61e08fe9ba23
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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