Imidazole → HCID 67060955, compound

HRID 401214Notes

Reaction equation

HRID 401214 reaction equation
[OH:1][C:2]1[C:12]([CH2:13][CH2:14][CH3:15])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21].N1C=CN=C1>CN(C=O)C>[Si:23]([O:1][C:2]1[C:12]([CH2:13][CH2:14][CH3:15])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17])([C:20]([CH3:22])([CH3:21])[CH3:19])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67060957HCID 67060957, compound

Product 1

HCID 67060955HCID 67060955, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of ethyl 4-hydroxy-3-nitro-5-propylbenzoate (1.5 g, 5.9 mmol), TBSCl (1.3 g, 8.9 mmol) and imidazole (800 mg, 11.8 mmol) in DMF (20 mL) was stirred at 30° C. overnight. A standard aqueous/EtOAc workup was followed by a purification by column chromatography (PE:EtOAc=15:1) to give product as a yellow oil (1.9 g, yield 86%).

Workup

  1. customA standard aqueous/EtOAc workup was followed by a purification by column chromatography (PE:EtOAc=15:1)

Sources & evidence

ORD record
ord-b7d3eed93c8342429138dee5ed8217d8
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

Loading…