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

HRID 1269361노트

반응식

HRID 1269361 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-aee082bad9f3440dbf63d25c9da2ab45
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199154B2

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