1,2-Dichloroethane → Methyl 4-[3-(1-adamantyl)benzoyl]butyrate

HRID 264778

反応式

HRID 264778 の反応式
[C:1]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl[C:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2.Cl.Cl[CH2:32]CCl>>[C:20]12([C:4]3[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=3)[C:1]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:32])=[O:13])=[O:8])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2

参加物

6

反応物 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 641541-ChloroadamantaneHCID 73914delta-Oxobenzenepentanoic acidHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 19036890Methyl 4-[3-(1-adamantyl)benzoyl]butyrate収率 24%

反応条件

温度
60 °C

実験手順

5.0 g (26.0 mmol) of 4-benzoylbutyric acid was dissolved in 100 ml of 1,2-dichloroethane, and 8.70 g (65.03 mmol) of aluminum trichloride and 5.30 (31.21 mmol) of 1-chloroadamantane were added thereto, followed by stirring the mixture at 60° C. for 6 hours. The reaction mixture was poured into hydrochloric acid, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. To the residue were added 100 ml of methanol and 5 ml of conc. sulfuric acid, and the mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, and the residue was poured into water, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica-gel column chromatography (eluent: a mixture of 1% ethyl acetate and hexane) to obtain 2.13 g of the above-mentioned compound (yield 24%).

後処理

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was then distilled off under reduced pressure
  4. additionTo the residue were added 100 ml of methanol and 5 ml of conc. sulfuric acid
  5. stirringthe mixture was stirred at room temperature overnight
  6. distillationThe solvent was distilled off under reduced pressure
  7. additionthe residue was poured into water
  8. extractionextracted with chloroform
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was then distilled off under reduced pressure
  11. customThe resulting residue was purified by silica-gel column chromatography (eluent
  12. additiona mixture of 1% ethyl acetate and hexane)

出典と根拠

ORDレコード
ord-3f0275be70ee491fa271079bb6395742
出典データセット
uspto-grants-1997_07
特許番号
US05646283

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