Methyl iodide → HCID 14698662, compound

Temperature

50 °C

Into dry tetrahydrofuran (20 ml) at 0° C. under anhydrous conditions was added slowly with stirring lithium diisopropylamide (2.67 g, 25 mmol) and then a solution of 4-(dimethyl-tert-butylsilyloxy)phenylacetic acid (2.66 g, 10 mmoles) in tetrahydrofuran (10 ml) was added dropwise. The resultant brown solution was stirred at 20°-25° C. for one hour and at 50° C. for 30 minutes. The solution was then cooled to 0° C. and methyl iodide (3.54 g, 25 mmol) was added dropwise. The reaction mixture was stirred at ambient temperature for about 16 hours and then quenched with saturated aqueous ammonium chloride (20 ml) and acidified with 3N hydrochloric acid. The reaction mixture was extracted with diethyl ether (3×100 ml) and the combined extracts washed with saturated aqueous sodium chloride (2×50 ml), dried over magnesium sulfate and the solvent removed in vacuo to afford a tan oil. The oil was chromatographed on a 5×15 cm column of silica gel eluted with 10 percent isopropanol/hexane to yield the desired product as a solid. m.p. 52°-4° C.

1. temperatureThe solution was then cooled to 0° C.
2. stirringThe reaction mixture was stirred at ambient temperature for about 16 hours
3. customquenched with saturated aqueous ammonium chloride (20 ml)
4. extractionThe reaction mixture was extracted with diethyl ether (3×100 ml)
5. washthe combined extracts washed with saturated aqueous sodium chloride (2×50 ml)
6. dry with materialdried over magnesium sulfate
7. customthe solvent removed in vacuo
8. customto afford a tan oil
9. customThe oil was chromatographed on a 5×15 cm column of silica gel
10. washeluted with 10 percent isopropanol/hexane

ORD record

ord-e4ada8f0109b44ababebd6a464b7586b

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04876366