1-Bromo-3-chloropropane → HCID 59651882、化合物

HRID 1186878ノート

反応式

HRID 1186878 の反応式
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH:6]([CH3:16])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[O:8])[CH3:2].Br[CH2:19][CH2:20][CH2:21][Cl:22].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH:6]([CH3:16])[C:7]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:19][CH2:20][CH2:21][Cl:22])=[CH:13][CH:14]=1)=[O:8])[CH3:2]

参加物

5

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 596519524-(4-Hydroxyphenyl)-3-methyl-4-oxo-butyric acid ethyl ester

生成物 1

HCID 59651882HCID 59651882、化合物収率 58.6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
60 °C

実験手順

A mixture of 4-(4-hydroxyphenyl)-3-methyl-4-oxo-butyric acid ethyl ester (12.5 g, 52.9 mmol), 1-bromo-3-chloropropane (11.3 mL, 114.6 mmol) and K2CO3 (21.9 g, 159 mmol) in acetone (200 mL) was stirred at 60° C. for 15 h. The reaction was cooled to RT and filtered over celite and the filtrate was evaporated at reduced pressure to give a crude residue. The crude residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution and the aqueous layer was extracted twice with methylene chloride. The combined organics was washed with brine, dried (Na2SO4), filtered, and concentrated to provide a crude product. The crude product was purified by ISCO (330 g) chromatography using 15% EtOAc in hexane to produce 4-[4-(3-chloro-propoxy)-phenyl]-3-methyl-4-oxo-butyric acid ethyl ester (9.7 g, 56%), MS m/z 267 (M-45).

後処理

  1. temperatureThe reaction was cooled to RT
  2. filtrationfiltered over celite
  3. customthe filtrate was evaporated at reduced pressure
  4. customto give a crude residue
  5. customThe crude residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution
  6. extractionthe aqueous layer was extracted twice with methylene chloride
  7. washThe combined organics was washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto provide a crude product
  12. customThe crude product was purified by ISCO (330 g) chromatography

出典と根拠

ORDレコード
ord-ba490a1ebf7d45f88e1d91f36caf13b3
出典データセット
uspto-grants-2014_03
特許番号
US08673916B2

反応ノート

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