Hydrochloric Acid → 1-(4-Methyl-2-thiazolyl)-2-(2-chloroethoxy)ethanol

Temperature

-30 °C

1.6 g of 4-methyl-2-formylthiazole was dissolved in 30 ml of tetrahydrofuran. The solution was cooled to -30° C. Thereto was dropwise added, in 10 minutes, 10 ml of a tetrahydrofuran solution containing 1.6M of 2-chloroethoxymethylmagnesium chloride. The mixture was stirred for 1 hour with ice cooling. The reaction mixture was added to a mixture of 50 ml of ice water, 50 ml of ethyl acetate and 2 g of ammonium chloride. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid and stirred at the same temperature for 5 minutes. The reaction mixture was adjusted to pH 6 with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distallation under reduced pressure. The residue thus obtained was pruned by column chromatography (eluant: toluene/ethyl acetate=4/1) to obtain 1.3 g of oily 1-(4-methyl-2-thiazolyl)-2-(2-chloroethoxy)ethanol.

1. additionThereto was dropwise added, in 10 minutes
2. stirringstirred at the same temperature for 5 minutes
3. customThe organic layer was separated
4. washwashed with water
5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
6. customThe solvent was removed by distallation under reduced pressure
7. customThe residue thus obtained

ORD record

ord-7700d77c66a3494a936678432408c88b

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05612381