Imidazole → 2-(tert-butyl-dimethyl-silanyloxy)-5-Nitrobenzoic acid methyl ester

HRID 884431

Reaction equation

HRID 884431 reaction equation
[N+:1]([C:4]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CN=C1.[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21].O>CN(C=O)C>[CH3:12][O:11][C:9](=[O:10])[C:8]1[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[O:14][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 87041Methyl 5-nitrosalicylate

Product 1

HCID 692965332-(tert-butyl-dimethyl-silanyloxy)-5-Nitrobenzoic acid methyl esterYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 5-nitrosalicylate (10.0 g, 50.7 mmol) and imidazole (3.8 g, 55.8 mol) in DMF (50 mL) at 0° C. was treated with t-butylchloro-dimethyl-silane and stirred 16 h at room temperature. The reaction mixture was poured into water (100 mL) and extracted with ether (3×50 mL). The combined extracts were washed with water (4×100 mL) and brine (50 mL), dried over magnesium sulfate, and concentrated. The crude residue was purified by flash chromatography (silica gel, 4×15 cm, eluted with 95/5 hexanes/EtOAc) to yield 2-(tert-butyl-dimethyl-silanyloxy)-5-nitro-benzoic acid methyl ester as a white solid (4.9 g, 31%).

Workup

  1. extractionextracted with ether (3×50 mL)
  2. washThe combined extracts were washed with water (4×100 mL) and brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography (silica gel, 4×15 cm, eluted with 95/5 hexanes/EtOAc)

Sources & evidence

ORD record
ord-8bf042a5a79b440899f682b6e4214cf9
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Linked notes

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