Butanal → 3-(2-Propenyl)-4-t-butyldimethylsilyloxy-2-(1-hydroxybutyl)cyclopentanone

HRID 35488

반응식

HRID 35488 반응식
C(P(CCCC)CCCC)CCC.[CH2:14]([Li])[CH:15]=[CH2:16].[Si:18]([O:25][CH:26]1[CH2:30][C:29](=[O:31])[CH:28]=[CH:27]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[CH:32](=[O:36])[CH2:33][CH2:34][CH3:35].[Cl-].[NH4+]>CCOCC.C(OCC)(=O)C.C1C=CC=CC=1>[CH2:14]([CH:27]1[CH:26]([O:25][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:30][C:29](=[O:31])[CH:28]1[CH:32]([OH:36])[CH2:33][CH2:34][CH3:35])[CH:15]=[CH2:16]

참가 물질

9

반응물 5

HCID 261ButanalHCID 13831TributylphosphineHCID 25517Ammonium ChlorideHCID 41316994-((tert-Butyl(dimethyl)silyl)oxy)cyclopent-2-en-1-oneHCID 178506856HCID 178506856, 화합물

생성물 1

HCID 212962343-(2-Propenyl)-4-t-butyldimethylsilyloxy-2-(1-hydroxybutyl)cyclopentanone수율 44%

시약·촉매·용매 3

HCID 241Benzene용매HCID 3283Diethyl Ether용매3회HCID 8857Ethyl Acetate용매

실험 절차

266 mg (2.2 mmoles) of 2-bromopropene was dissolved in 5 ml of dry ether, and the solution was cooled to -95° C. Then, 3.0 ml (4.8 mmoles) of t-butyllithium (as 1.60M pentane solution) was added, and the mixture was stirred at -78° C. for 2 hours to form a 2-propenyllithium solution. 300 mg (2.05 mmoles) of cuprous iodide was taken into a reaction vessel. The reaction vessel was purged with argon, and 30 ml of dry ether and 1.02 ml (4.1 mmoles) of tributyl phosphine were added. The mixture was stirred for 10 minutes. The mixture was added to the 2-propenyllithium solution prepared above, and the mixture was stirred for 5 minutes. A solution of 425 mg (2.0 mmoles) of 4-t-butyldimethylsilyloxy-2-cyclopentenone in 5 ml of dry ether was added. The mixture was stirred at -78° C. for 10 minutes and -40° C. for 20 minutes. A solution of 148 mg (2.05 mmoles) of butanal in 5 ml of dry ether was added, and the mixture was stirred at -40° C. for 1 hour. 50 ml of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ether. The etheric layers were combined, dried over anhydrous magnesium sulfate, filtered, concentrated and then subjected to silica gel column chromatography (silica gel 50 g; eluent, benzene:ethyl acetate=10:1→3:1 to give 287 mg (yield 44%) of 3-(2-propenyl)-4-t-butyldimethylsilyloxy-2-(1-hydroxybutyl)cyclopentanone. The resulting compound had the following spectral data.

후처리

  1. additionwere added
  2. customprepared above, and the mixture
  3. stirringwas stirred for 5 minutes
  4. stirringThe mixture was stirred at -78° C. for 10 minutes and -40° C. for 20 minutes
  5. stirringthe mixture was stirred at -40° C. for 1 hour
  6. extractionthe mixture was extracted with ether
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9557bcdf92b34f94adc10514da842f42
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766147

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