Boron trifluoride etherate → HCID 86754119, compound

To a solution of methyl phenyl sulfone (470 mg, 3.0 mmole) in dry THF (10.0 mL) at -78° C. was dropwise added n-BuLi (1.2 mL, 3.0 mmole, 2.5 M solution in hexanes) under nitrogen and the resulting mixture was stirred at this temperature for 30 min followed by the addition of boron trifluoride diethyl etherate (0.092 mL, 1.0 mmole). A solution of the THR-epoxide (234 mg, 1.0 mmole) in dry THF (5.0 mL) was added and the resulting mixture was stirred at -78° C. for 3 h and quenched with saturated ammonium chloride (5.0 mL). The product was extracted with EtOAc (3×20 mL) and the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, and concentrated using rotatory evaporation. The oily residue was purified by flash column chromatography (hexane/EtOAc=1/1) to yield 370 mg (95%) of the desired product as a colorless oil. This material (307 mg, 0.787 mmole) was then dissolved in dry dichloromethane (15 mL) and cooled down to 0° C. N-N-diisopropylethylamine (0.82 mL, 4.7 mmole) and chloromethyl methyl ether (0.15 mL, 2.0 mmole) were added and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was concentrated using rotary evaporation and the oily residue was purified by flash column chromatography (hexane/EtOAc=2/1) to yield 325 mg (95%) of the desired protected alcohol as a colorless oil.

1. customat -78° C.
2. stirringthe resulting mixture was stirred at -78° C. for 3 h
3. customquenched with saturated ammonium chloride (5.0 mL)
4. extractionThe product was extracted with EtOAc (3×20 mL)
5. washthe combined organic extracts were washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated
8. customevaporation
9. customThe oily residue was purified by flash column chromatography (hexane/EtOAc=1/1)

ORD record

ord-596cf14f560d45ef85486833e48303ab

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05914410