Imidazole → Benzoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester

HRID 1699739Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.53 g of 3-hydroxybenzoic acid methyl ester and 1.69 g of imidazole were placed in a 50 ml flask, and a gas in the reaction system was replaced with nitrogen. 5 ml of DMF was added into the flask and stirred at 0° C. The obtained solution was mixed with 1.57 g of t-butyldimethylsilyl chloride, heated up to room temperature, simultaneously stirred overnight, and then mixed with a saturated aqueous solution of ammonium chloride to stop the reaction. The reaction solution was extracted with diethyl ether, and the obtained organic layer was sequentially washed with water, a saturated aqueous solution of potassium hydrogen sulfate and a saturated aqueous solution of sodium chloride and then dried over magnesium sulfate. The solvent was distilled away under reduced pressure to obtain 1.69 g of the title compound. Yield: 98%.

Workup

temperatureheated up to room temperature, simultaneously stirred overnight
customthe reaction
extractionThe reaction solution was extracted with diethyl ether
washthe obtained organic layer was sequentially washed with water
dry with materiala saturated aqueous solution of potassium hydrogen sulfate and a saturated aqueous solution of sodium chloride and then dried over magnesium sulfate
distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record: ord-2e9693b4154849e39a7da7d17050cc96
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348478B1

Reaction notes

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