Dimethylformamide → HCID 58337199, compound

Temperature

50 °C

A mixture of 5-hydroxy-2-iodoanisole (Reference Compound No. 5, 4.30 g, 17.2 mmol), chlorodimethylether (2.46 mL, 32.4 mmol), and potassium carbonate (5.94 g, 43.0 mmol) was suspended in anhydrous N,N-dimethylformamide (80 mL) and stirred at 50° C. for 1.5 hours. After cooling down, the reaction mixture was diluted with ethyl acetate (100 mL) and diethylether (200 mL). It was washed with water (300 mL), then the aqueous layer was extracted with diethylether (100 mL). After the organic layers were combined, it was washed with water (200 mL, twice) and saturated brine (100 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (958 mg) as a colorless oil. (Yield 19%)

1. temperatureAfter cooling down
2. washIt was washed with water (300 mL)
3. extractionthe aqueous layer was extracted with diethylether (100 mL)
4. washit was washed with water (200 mL
5. dry with materialtwice) and saturated brine (100 mL) successively, dried over anhydrous magnesium sulfate
6. customthe solvent was removed under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

ORD record

ord-2951aa042de94e5eb5f3b12cced60c7c

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08664221B2