Diethyl Ether → Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

HRID 1987830노트

반응식

HRID 1987830 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.[NH4+].[Cl-].CCOCC>C1COCC1>[Si:35]([O:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([OH:26])=[CH:28][CH:29]=1)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 108935701-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]benzene

생성물 1

HCID 11230163Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Tetrabutylammonium fluoride (1 M THF, 44 mL, 44 mmol) was added to a 0° C. solution of 1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene (14 g, 40 mmol) in THF (400 mL). The reaction was stirred for 30 minutes, then poured into a mixture of saturated NH4Cl and Et2O. The layers were separated and the aqueous phase was extracted twice with Et2O. The organics were combined, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was chromatographed (1:9 EtOAc/hexanes) to provide the product as a colorless oil (8.0 g, 85%).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted twice with Et2O
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed (1:9 EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ba6191afb576451498c86c9e182ba568
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553842B2

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