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

HRID 1269361Notes

Reaction equation

HRID 1269361 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-aee082bad9f3440dbf63d25c9da2ab45
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

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