3-Acetoxy-5-t-butyldimethylsiloxycyclopent-1-ene → 2-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 2163166

반응식

HRID 2163166 반응식
C([O:4][CH:5]1[CH2:9][CH:8]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:7]=[CH:6]1)(=O)C>CO.[OH-].[Ba+2].[OH-]>[O:10]([CH:8]1[CH2:9][CH:5]([OH:4])[CH:6]=[CH:7]1)[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

참가 물질

4

반응물 1

HCID 127633543-Acetoxy-5-t-butyldimethylsiloxycyclopent-1-ene

생성물 1

HCID 127633552-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-수율 45%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6093286Barium hydroxide용매

실험 절차

Two hundred milligrams (0.78 mmol) of 3-acetoxy-5-t-butyldimethylsiloxycyclopent-1-ene was dissolved in 1.0 milliliter of a methanol solution of 1 normal barium hydroxide, after which the resulting solution was heated under reflux for 15 minutes in an atmosphere of nitrogen. The methanol was then distilled off under reduced pressure, after which ethanol was added to precipitate a solid, which was filtered off. Ehtanol was then distilled off from the filtrate, after which the concentrated residue was extracted with ether after addition of water thereto. The resulting organic layer was then thoroughly washed in water, dried with anhydrous sodium sulfate and thereafter concentrated to obtain a crude product. The so obtained product was then separated by preparative thin-layer chromatography (silica gel 2mm, hexane:ethyl acetate = 4:1) to obtain 75 milligrams (0.35 mmol, 45%) of 3-t-butyldimethylsiloxy-5-hydroxycyclopent-1-ene.

후처리

  1. temperatureafter which the resulting solution was heated
  2. temperatureunder reflux for 15 minutes in an atmosphere of nitrogen
  3. distillationThe methanol was then distilled off under reduced pressure
  4. additionafter which ethanol was added
  5. customto precipitate a solid, which
  6. filtrationwas filtered off
  7. distillationEhtanol was then distilled off from the filtrate
  8. extractionafter which the concentrated residue was extracted with ether
  9. additionafter addition of water
  10. washThe resulting organic layer was then thoroughly washed in water
  11. dry with materialdried with anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customto obtain a crude product
  14. customThe so obtained product
  15. customwas then separated by preparative thin-layer chromatography (silica gel 2mm, hexane:ethyl acetate = 4:1)

출처 및 근거

ORD 기록
ord-a9b699adecf641e7b10c0a847e936b15
출처 데이터셋
uspto-grants-1979_01
특허 번호
US04132726

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