Hydrochloric Acid → HCID 86031668, compound

Temperature

0 °C

This ketone (1.3 g, 6.1 mmol) was dissolved in dichloromethane (40 mL), then TEA (5.1 mL, 36.6 mmol) and tert-butyl-dimethyl-trifluoro methansulphonate (4.2 mL, 18.3 mmol) were added. The orange solution was stirred overnight, then diluted with more dichloromethane (150 mL), washed twice with a 5% sodium hydrogencarbonate solution (50 mL), with water, with brine, then dried over sodium sulphate and concentrated to give the bis-silylated derivative (2.67 g). To half of the material (1.32 g, 2.94 mmol) dissolved in tetrahydrofuran (THF, 25 mL) and cooled to 0° C., a solution of NBS (0.549 g, 3.09 mmol) in THF (10 mL) was added dropwise in 5 minutes. The reaction mixture was stirred at 0° C. for 1 hour, then 2 N HCl was added and the reaction mixture was stirred for 24 hours at r.t. The crude was purified by flash chromatography (eluant: hexane/ethyl acetate 5:1) to yield 0.325 g of title compound.

1. washwashed twice with a 5% sodium hydrogencarbonate solution (50 mL), with water, with brine
2. dry with materialdried over sodium sulphate
3. concentrationconcentrated
4. customto give the bis-silylated derivative (2.67 g)
5. stirringThe reaction mixture was stirred at 0° C. for 1 hour
6. stirringthe reaction mixture was stirred for 24 hours at r.t
7. customThe crude was purified by flash chromatography (eluant: hexane/ethyl acetate 5:1)

ORD record

ord-b02f77649126462496b429eca3d6ef0b

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279575B2