Benzyl Bromide → HCID 10583327, compound

n-BuLi (1.8 mL, 4.51 mmol, 2.5 M in hexane) was added to a solution of 2-methylfuran (0.37 mL, 4.10 mmol) in anhydrous THF (3 mL) at −25° C. The resulting solution was stirred at room temperature for 3 h and then cooled to −15° C. Benzyl bromide (0.59 mL, 4.92 mmol), which was passed through a plug of aluminum oxide, was added and the solution was warmed to rt and stirred overnight. Saturated NH4Cl solution (5 mL) was added and the mixture was stirred for 1 h. The reaction mixture was then extracted with ether (2×5 mL) and the combined organic extracts were dried and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with hexanes gave 323 mg (1.88 mmol, 46%) of compound 205A as colorless oil. HPLC: 95% at 3.72 min (retention time) (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) and about 400 mg mixture of product and benzyl bromide (˜2:1 by HPLC).

1. temperaturecooled to −15° C
2. additionwas added
3. temperaturethe solution was warmed to rt
4. stirringstirred overnight
5. stirringthe mixture was stirred for 1 h
6. extractionThe reaction mixture was then extracted with ether (2×5 mL)
7. customthe combined organic extracts were dried
8. concentrationconcentrated under reduced pressure
9. customPurification by flash chromatography on silica gel eluting with hexanes

ORD record

ord-4f9d49d1c5ef4984b389830ea4a66f83

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07655689B2