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

HRID 429930Notes

Reaction equation

HRID 429930 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:2])[CH3:3]

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-e8d7d93f52794e82922bcd0040ee46cd
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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