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

HRID 44584

반응식

HRID 44584 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 1383222-Cyclohexenone, 5,5-dimethyl-

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4dd83782f0c64288adf2d0e252601348
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541429B2

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