Imidazole → Methyl 5-((tert-butyldimethylsilyl)oxy)-2-hydroxybenzoate

HRID 637217Notes

Reaction equation

HRID 637217 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>ClCCl>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 75077Methyl Gentisate

Product 1

HCID 18465044Methyl 5-((tert-butyldimethylsilyl)oxy)-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine methyl 2,5-dihydroxybenzoate (8.45 g, 50.2 mmol), imidazole (4.1 g, 60.3 mmol), and t-butyldimethylsilyl chloride (9.09 g, 60.3 mmol) in dichloromethane (100 mL). After 30 minutes, dilute the reaction mixture with dichloromethane (100 mL) and extract with water. Dry the organic layer over MgSO4, filter and evaporate in vacuo to give methyl 2-hydroxy-5-(t-butyldimethylsilyloxy)benzoate.

Workup

  1. extractionextract with water
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo

Sources & evidence

ORD record
ord-7966a61a3fc144298905f3cb18b65896
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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