Methyl iodide → HCID 86690143, compound

Temperature

-78 °C

Under argon condition, tert-butyl((4-ethynylbenzyl)oxy)dimethyl-silane (247 mg, 1.00 mmol) was dissolved in 5 mL of dry THF, cooled to −78° C., and n-butyl lithium (805 μL, 2.49 M solution in n-hexane, 2.00 mmol) was slowly added thereto. After stirring for 20 minutes at −78° C., iodomethane (313 μL, 5.00 mmol) was added again thereto. Thereafter, the temperature was raised to room temperature and the reaction mixture was stirred for 30 minutes at room temperature. Upon completion of the reaction, the reaction was terminated by adding 10 mL of aqueous saturated ammonium chloride solution. The reaction mixture was extracted with ethyl acetate (5 mL×4) and the organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out, and the resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 253 mg (0.971 mmol, 97%) of the desired compound.

1. temperatureThereafter, the temperature was raised to room temperature
2. stirringthe reaction mixture was stirred for 30 minutes at room temperature
3. customUpon completion of the reaction
4. customthe reaction was terminated
5. additionby adding 10 mL of aqueous saturated ammonium chloride solution
6. extractionThe reaction mixture was extracted with ethyl acetate (5 mL×4)
7. customthe organic layer thus obtained
8. customto remove water
9. filtrationThe precipitate was filtered out
10. concentrationthe resulting solution was concentrated by distillation under reduced pressure
11. custompurified by column chromatography

ORD record

ord-e85ee47b84294ee3892963a518662d2b

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809012B2