Imidazole → Tert-butyl(5-methoxy-2-nitrobenzyloxy)dimethylsilane

HRID 1627683Notes

Reaction equation

HRID 1627683 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH2:9][OH:10])[CH:8]=1.N1C=CN=C1.[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C1COCC1.CN(C=O)C>[C:20]([Si:23]([O:10][CH2:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[N+:11]([O-:13])=[O:12])([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:19]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 53405061(5-Methoxy-2-nitrophenyl)methanol

Product 1

HCID 66980104Tert-butyl(5-methoxy-2-nitrobenzyloxy)dimethylsilaneYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of (5-methoxy-2-nitrophenyl)methanol (12.0 g, 65.6 mmol) in anhydrous THF (200 mL) and DMF (20 mL) was added imidazole (9.80 g, 144 mmol). Then TBSCl (11.8 g, 78.6 mmol) was added portionwise at 0° C. and the mixture was stirred at 30° C. for 2 hours. The mixture was quenched with ice-water (100 mL). An EtOAc workup was followed by removal of solvent in vacuo and purification by column chromatography (PE/EtOAc=10/1) to give the product (16.0 g, yield 84%) as a yellow oil.

Workup

  1. customThe mixture was quenched with ice-water (100 mL)
  2. customAn EtOAc workup was followed by removal of solvent in vacuo and purification by column chromatography (PE/EtOAc=10/1)

Sources & evidence

ORD record
ord-2ed6e0ac2e9d4f2c89a8575b33ecee09
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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