Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]- → HCID 21898100, 화합물

HRID 2099145노트

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HRID 2099145 반응식
[CH2:1]([Li])CCC.[C:6]([Si:10]([CH3:22])([CH3:21])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH3:19])=[CH:14][CH:13]=1)([CH3:9])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:6]([Si:10]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:1])=[CH2:19])=[CH:14][CH:13]=1)([CH3:22])[CH3:21])([CH3:9])([CH3:8])[CH3:7]

참가 물질

5

반응물 2

HCID 10857908Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-HCID 178418339Butyllithium

생성물 1

HCID 21898100HCID 21898100, 화합물수율 84.1%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매

실험 절차

Methyl(triphenylphosphonium) bromide (17.1 g, 48.0 mmol) was suspended in THF (96 mL) and cooled to 0° C. n-Butyllithium (2.5 M in hexane, 19.2 mL, 48.0 mmol) was added dropwise to the mixture. The red solution was stirred at rt for 0.5 h. 1-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-ethanone (10.0 g, 40.0 mmol) was added. The solution turned bright yellow and a white precipitate formed. The mixture was stirred for 1 h at rt and then the solution was quenched with saturated NaHCO3. The aqueous phase was extracted with diethyl ether and the combined organic layers were washed with saturated NaHCO3. The organic layers were dried over sodium sulfate, filtered and concentrated. The resultant mixture was eluted through a plug of silica gel (hexanes) and the filtrate was concentrated to provide tert-butyl-(4-isopropenyl-phenoxy)-dimethyl-silane (8.36 g, 84%) as a colorless oil. ESI MS (m/z 249, M+H).

후처리

  1. additionwas added dropwise to the mixture
  2. customa white precipitate formed
  3. stirringThe mixture was stirred for 1 h at rt
  4. customthe solution was quenched with saturated NaHCO3
  5. extractionThe aqueous phase was extracted with diethyl ether
  6. washthe combined organic layers were washed with saturated NaHCO3
  7. dry with materialThe organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washThe resultant mixture was eluted through a plug of silica gel (hexanes)
  11. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-bafcb8acfc31476e80bb38bca7a4a33d
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569568B2

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