Ethyl Acetate → HCID 178447882、化合物

HRID 1646471ノート

反応式

HRID 1646471 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[CH2:7]([C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]2[CH:24]=[CH:23][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=2)[CH2:14][CH2:15]1)[CH2:8][CH3:9]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178447883HCID 178447883、化合物

生成物 1

HCID 178447882HCID 178447882、化合物収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Into a three-necked flask having a 1 l capacity was added lithium aluminum hydride (5.7 g, 0.15 mol), and cooled down to 0° C., followed by dropwise adding tetrahydrofuran (100 ml) and a solution of 4-(trans-4'-n-propylcyclohexyl)benzoyl chloride (53.0 g, 0.2 mol) in tetrahydrofuran (100 ml) in this order, agitating the mixture at room temperature for 3 hours, again cooling it down to 0° C., adding ethyl acetate (10 ml), water (10 ml) and 2N NaOH aqueous solution (10 ml) in this order, heating the mixture under reflux for 30 minutes, cooling the resulting material, filtering, adding saturated NaCl aqueous solution (100 ml) and ethyl acetate (100 ml), removing the aqueous layer, washing the resulting organic layer with water till the washing water became neutral, drying over anhydrous sodium sulfate, removing a drying agent, concentrating under reduced pressure, recrystallizing from heptane solvent and drying to obtain the captioned compound (35.8 g). Its structure was confirmed by NMR spectra.

後処理

  1. customInto a three-necked flask having
  2. temperatureagain cooling it down to 0° C.
  3. temperatureheating the mixture
  4. temperatureunder reflux for 30 minutes
  5. temperaturecooling the resulting material
  6. filtrationfiltering
  7. additionadding saturated NaCl aqueous solution (100 ml) and ethyl acetate (100 ml)
  8. customremoving the aqueous layer
  9. washwashing the resulting organic layer with water till the washing water
  10. dry with materialdrying over anhydrous sodium sulfate
  11. customremoving a drying agent
  12. concentrationconcentrating under reduced pressure
  13. customrecrystallizing from heptane solvent
  14. customdrying

出典と根拠

ORDレコード
ord-14596ad17cd741afa9e9211ac1f96d61
出典データセット
uspto-grants-1993_01
特許番号
US05180519

反応ノート

読み込み中…