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

HRID 2230679Notes

Reaction equation

HRID 2230679 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-fe96684f2fea4a8c89fc881da0399e13
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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