Hydrochloric Acid → 4-(3-Bromo-4-methoxy-phenyl)-4-methyl-3-oxo-pentanoic acid ethyl ester

HRID 61811

反応式

HRID 61811 の反応式
CS(O)(=O)=[O:3].[Br:6][C:7]1[CH:8]=[C:9]([C:15]([CH3:19])([CH3:18])[C:16]#N)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].[C:20]([O:23][CH2:24][CH2:25]Br)(=[O:22])[CH3:21].Cl>[Zn].C1COCC1>[CH2:24]([O:23][C:20](=[O:22])[CH2:21][C:16](=[O:3])[C:15]([C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([Br:6])[CH:8]=1)([CH3:19])[CH3:18])[CH3:25]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 135641-Acetoxy-2-bromoethaneHCID 113688102-(3-Bromo-4-methoxyphenyl)-2-methylpropionitrile

生成物 1

HCID 668346654-(3-Bromo-4-methoxy-phenyl)-4-methyl-3-oxo-pentanoic acid ethyl ester収率 72%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
80 °C

実験手順

To the THF suspension of zinc (5.72 g, 2 eq.), methanesulfonic acid (25.6 μl, 0.01 eq.) was added, and then stirred at 80° C. for 10 min. Then, the THF solution of 2-(3-bromo-4-methoxy-phenyl)-2-methyl-propionitrile (10 g, 39.35 mmol) was added, followed by addition of bromoethyl acetate (11.07 ml, 1.6 eq.) over 1 hr. The mixture was further stirred for 30 min. To the reaction solution, 4 M hydrochloric acid was added, and stirred at room temperature overnight. After extraction with ethyl acetate, the organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (orange oily substance, 9.74 g, 72%).

後処理

  1. additionwas added
  2. stirringThe mixture was further stirred for 30 min
  3. stirringstirred at room temperature overnight
  4. extractionAfter extraction with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe drying agent was removed by filtration
  8. customthe residues obtained
  9. concentrationafter concentration under reduced pressure
  10. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-e3caf457cc424c3a82933351d7c7f175
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

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