Methyl iodide → HCID 22144774, compound

Temperature

-78 °C

A solution of 0.17 gm (0.71 mMol) ethyl 2-(5-fluorobenzofur-7-yl)propionate (EXAMPLE 39) in 2.5 mL tetrahydrofuran was cooled to −78° C. To this solution were added 0.89 mL (0.89 mmol) lithium bis(trimethylsilyl)amide (1.0 M in hexane). After stirring at −78° C. for 1 hour, the reaction mixture was quenched by the addition of 0.13 mL (2.13 mMol) iodomethane. The reaction mixture was allowed to warm to room temperature and was diluted with ethyl acetate. This mixture was then washed sequentially with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The remaining organics were concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with hexane containing 20% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 0.16 gm (90%) of the desired compound.

1. temperatureto warm to room temperature
2. washThis mixture was then washed sequentially with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
3. concentrationThe remaining organics were concentrated under reduced pressure
4. washeluting with hexane containing 20% ethyl acetate
5. additionFractions containing product
6. concentrationconcentrated under reduced pressure

ORD record

ord-2663cd03f7b640c5b43e41ddcb30406f

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07045545B1