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

HRID 1987830ノート

反応式

HRID 1987830 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ba6191afb576451498c86c9e182ba568
出典データセット
uspto-grants-2009_06
特許番号
US07553842B2

反応ノート

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