Bromomethyl 4-methoxyphenyl ketone → Diethyl alpha-(4-methoxyphenacyl)malonate

HRID 1415822ノート

反応式

HRID 1415822 の反応式
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC(C)([O-])C.[K+].[CH3:18][O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24](=[O:27])[CH2:25]Br)=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:18][O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24](=[O:27])[CH2:25][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 7761Diethyl MalonateHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 21862838Diethyl alpha-(4-methoxyphenacyl)malonate収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3.50 g (21.8 mmol) of diethyl malonate were dissolved in 60 ml of anhydrous tetrahydrofuran, and 2.70 g (24.0 mmol) of potassium t-butoxide were added to the resulting solution, whilst ice-cooling. The mixture was then stirred for 1 hour. At the end of this time, a solution of 5.00 g (21.8 mmol) of 4-methoxyphenacyl bromide in 40 ml of anhydrous tetrahydrofuran was slowly added dropwise to the mixture, whilst ice-cooling. The mixture was stirred, whilst ice-cooling for 1 hour, and then a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 1:4 by volume mixture of ethyl acetate and hexane, to give 4.87 g of the title compound as a slightly yellow oily substance (yield 73%).

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe mixture was stirred, whilst ice-
  4. temperaturecooling for 1 hour
  5. extractionthe mixture was extracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed by distillation under reduced pressure
  10. customThe residue thus obtained
  11. washeluted with a 1:4 by volume mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-a3ff395e85bd4ee4b515154a5db5ae0b
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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