Imidazole → Methyl 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzoate

HRID 369820Notes

Reaction equation

HRID 369820 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C>[C:11]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:3]([O:2][CH3:1])=[O:15])([CH3:12])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 13207060Methyl 3-tert-butyl-4-hydroxybenzoate

Product 1

HCID 18352492Methyl 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzoateYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to example 183, 5.00 g of methyl-3-tert-butyl-4-hydroxybenzoate was silylated using 4.34 g of tert-butyldimethylsilyl chloride, 3.59 g of imidazole, and 70 mL of anhydrous DMF. The crude product was purified by flash chromatography on silica gel (9:1 hexane:EtOAc) to afford 6.1 g (79%) of methyl 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzoate as a clear liquid.

Workup

  1. customThe crude product was purified by flash chromatography on silica gel (9:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-0df66ba1a0f44097b4e91d1c71d4442e
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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