Sodium Hydroxide → HCID 58223409, compound

Participants

Reaction Conditions

Reaction Steps

To tetrahydrofuran (20 mL) was added dropwise titanium tetrachloride (1.10 mL, 10.1 mmol) at −78° C., and the mixture was stirred for 10 minutes. At the same temperature, a tetrahydrofuran (20 mL) solution of lithium aluminum hydride (767 mg, 20.1 mmol) was gradually added dropwise and stirred for 30 minutes. To the mixture was added 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-(methylsulfonyl)pyrazolo[5,1-b][1,3]thiazole (384 mg, 1.01 mmol), and the mixture was stirred at room temperature for 30 minutes. The mixture was heated at 50° C. for one hour. After the reaction was completed, 5N sodium hydroxide was gradually added dropwise while cooling on ice to stop the reaction. The reaction mixture was filtered with Celite and extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate=1/1) to obtain the title compound (32.8 mg, 0.094 mmol).

Provenance & Evidence