2-Cyclohexen-1-one, 3-methoxy-5,5-dimethyl- → 2-Cyclohexenone, 5,5-dimethyl-

HRID 44584

反応式

HRID 44584 の反応式
C[O:2][C:3]1[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5](=O)[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:9][C:7]1([CH3:10])[CH2:8][C:3](=[O:2])[CH:4]=[CH:5][CH2:6]1

参加物

4

反応物 2

HCID 1383182-Cyclohexen-1-one, 3-methoxy-5,5-dimethyl-HCID 21226445Aluminium lithium hydride

生成物 1

HCID 1383222-Cyclohexenone, 5,5-dimethyl-

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 3-methoxy-5,5-dimethyl-cyclohex-2-enone (80 g, 0.52 mol) in anhydrous tetrahydrofuran (270 mL) was treated dropwise with a 1M solution of LiAlH4 in tetrahydrofuran (182 mL), under argon atmosphere and keeping the temperature of the reaction between 0° C. and 5° C. The temperature was allowed to rise to 25° C. and the mixture was stirred for 4 hours. The resulting slurry was cooled with an ice bath, quenched with ethyl acetate (30 mL) and poured with caution into a cooled 2 M H2SO4 solution. The aqueous solution was then extracted with diethyl ether (300 mL×3), dried on Na2SO4 and evaporated under reduced pressure to remove most of the solvent. The crude material contained the title compound as a low boiling point oil that was used in the next step without further purification.

後処理

  1. customthe temperature of the reaction between 0° C. and 5° C
  2. customto rise to 25° C.
  3. temperatureThe resulting slurry was cooled with an ice bath
  4. customquenched with ethyl acetate (30 mL)
  5. additionpoured with caution into a cooled 2 M H2SO4 solution
  6. extractionThe aqueous solution was then extracted with diethyl ether (300 mL×3)
  7. customdried on Na2SO4
  8. customevaporated under reduced pressure
  9. customto remove most of the solvent
  10. customwas used in the next step without further purification

出典と根拠

ORDレコード
ord-4dd83782f0c64288adf2d0e252601348
出典データセット
uspto-grants-2013_09
特許番号
US08541429B2

関連ノート

読み込み中…