Diiodomethane → Methyl 3-(2-cyclopropyl-1-hydroxyethyl)-4-methylbenzoate

Temperature

2.5 °C

Into a 100-mL 3-necked round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 3-(1-hydroxybut-3-en-1-yl)-4-methylbenzoate (compound 4.3, 50 mg, 0.23 mmol). Diethylzinc (1 M in toluene) (3.45 mL, 3.45 mmol) in toluene (10 mL) was added and the mixture was cooled to 0-5° C., then diiodomethane (924 mg, 3.45 mmol) was added drop-wise. The resulting mixture was stirred for 2 h at room temperature, then carefully quenched with 1 M aqueous HCl (50 mL) and diluted with MTBE (50 mL). The aqueous phase was extracted with MTBE (3×20 mL) and the combined organics was washed with saturated sodium bicarbonate (2×20 mL), brine (2×20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:3) as the eluent to yield the title compound as a yellow oil (40 mg, 74%).

1. customInto a 100-mL 3-necked round-bottom flask, which was purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customcarefully quenched with 1 M aqueous HCl (50 mL)
4. additiondiluted with MTBE (50 mL)
5. extractionThe aqueous phase was extracted with MTBE (3×20 mL)
6. washthe combined organics was washed with saturated sodium bicarbonate (2×20 mL), brine (2×20 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:3) as the eluent

ORD record

ord-6be646fc34f141b9b2c6f7fd5ffa82cb

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2