3-Hydroxybenzyl alcohol → 3-((((1,1-Dimethylethyl)dimethylsilyl)oxy)methyl)phenol

HRID 1269361ノート

反応式

HRID 1269361 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.N1C=CN=C1.[C:15]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[Si:19]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 1023-Hydroxybenzyl alcoholHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 149405563-((((1,1-Dimethylethyl)dimethylsilyl)oxy)methyl)phenol収率 92.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 79 g of 3-(hydroxymethyl)phenol in 300 mL of DMF cooled at 0° C. was added 50 g of imidazole followed by 101 g of tert-butyl(chloro)dimethylsilane. The reaction was warmed to rt and stirred overnight. The reaction was quenched with aqueous NH4Cl, extracted with EtOAc and washed with brine, dried over sodium sulfate, evaporated, and purified by flash chromatography (10–30% EtOAc/hexane) to afford 140 g of the title compound as a yellow oil.

後処理

  1. customThe reaction was quenched with aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. custompurified by flash chromatography (10–30% EtOAc/hexane)

出典と根拠

ORDレコード
ord-aee082bad9f3440dbf63d25c9da2ab45
出典データセット
uspto-grants-2007_04
特許番号
US07199154B2

反応ノート

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