Hydroquinone → 4-(tert-Butyldimethylsiloxy)phenol

HRID 68209ノート

反応式

HRID 68209 の反応式
N1C=CN=C1.[C:6]1([CH:13]=[CH:12][C:10]([OH:11])=[CH:9][CH:8]=1)[OH:7].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C)C=O.O>[Si:14]([O:7][C:6]1[CH:13]=[CH:12][C:10]([OH:11])=[CH:9][CH:8]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

参加物

6

反応物 3

HCID 785HydroquinoneHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 5973884-(tert-Butyldimethylsiloxy)phenol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2.9 parts of imidazole, 1.99 parts of hydroquinone and 3 parts of tert-butyldimethylsilyl chloride in 10 mL of dimethylformamide was stirred at room temperature for 1 hr 45 min. The reaction was monitored by TLC showed formation of product. The reaction mixture was diluted with 50 mL of deionized water and product was extracted with 2×50 mL of ether. The combined organic layer was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography on silica gel with 5% ethyl acetate-hexanes to yield 2.24 parts 4-(tert-butyldimethylsilyloxy)phenol. NMR was used to confirm the following structure.

後処理

  1. extractionwas extracted with 2×50 mL of ether
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by column chromatography on silica gel with 5% ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-92c3430aed074b879487da802bcbe81f
出典データセット
uspto-grants-2014_09
特許番号
US08822233B2

反応ノート

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