Hydrochloric Acid → 4-Cyano-4-(3-cyano-5-thienyl)-5-methylhexanol

HRID 1071625노트

반응식

HRID 1071625 반응식
[C:1]([C:3]([C:14]1[S:18][CH:17]=[C:16]([C:19]#[N:20])[CH:15]=1)([CH:11]([CH3:13])[CH3:12])[CH2:4][CH2:5][C:6](OCC)=[O:7])#[N:2].[BH4-].[Li+].Cl.O>C1COCC1>[C:1]([C:3]([C:14]1[S:18][CH:17]=[C:16]([C:19]#[N:20])[CH:15]=1)([CH:11]([CH3:13])[CH3:12])[CH2:4][CH2:5][CH2:6][OH:7])#[N:2]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 22393597Ethyl 4-cyano-4-(3-cyano-5-thienyl)-5-methylhexanate

생성물 1

HCID 223935934-Cyano-4-(3-cyano-5-thienyl)-5-methylhexanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl 4-cyano-4-(3-cyano-5-thienyl)-5-methylhexanate (0.55 g) was dissolved in THF (10 ml), lithium borohydride (46 mg) was added, and the mixture was heated under reflux for 1.5 hours. After cooling as it was to room temperature, 1N aqueous hydrochloric acid and water were added at 0° C., and the mixture was extracted with ethyl acetate. The mixture was further washed with brine, dried over anhydrous magnesium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system), to give the title compound pale as a yellow oil (1.25 g, 47%). Further, the catalyst was filtered off, and the filtrate was evaporated. The resulting residue was purified by preparative thin layer silica gel column chromatography (hexane/ethyl acetate system), to give the title compound as a pale yellow oil (0.39 g, 83%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling as it
  4. customwas to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe mixture was further washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

출처 및 근거

ORD 기록
ord-b235a9e760fc4c7299c81c7bef341694
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906072B1

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