Methyl iodide → HCID 21195981, compound

Temperature

-78 °C

A solution of 4-(2-fluoro-5-bromobenzyloxy)-but-2-ynyl alcohol (1.07 g, 3.92 mmol) in tetrahydrofuran (26 ml) was cooled to −40° C. and then treated with potassium t-butoxide (4.31 ml of a 1 M solution in tetrahydrofuran, 4.31 mmol). The resulting dark orange solution was stirred for thirty minutes, cooled to −78° C. and treated with methyl iodide (0.49 ml, 7.84 mmol). The reaction was warmed to 0° C. and stirred for 1.5 hours. The reaction mixture was then partitioned between methylene chloride and saturated sodium bicarbonate. The organic fraction was dried over sodium sulfate, and the solvents were removed in vacuo. The desired title intermediate was further purified by high performance liquid chromatography to yield 790 mg (70%) as a clear oil.

1. temperatureThe reaction was warmed to 0° C.
2. stirringstirred for 1.5 hours
3. customThe reaction mixture was then partitioned between methylene chloride and saturated sodium bicarbonate
4. dry with materialThe organic fraction was dried over sodium sulfate
5. customthe solvents were removed in vacuo
6. customThe desired title intermediate was further purified by high performance liquid chromatography
7. customto yield 790 mg (70%) as a clear oil

ORD record

ord-474ea3ca761b43fa8246b4cafd5bc7e2

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1