Potassium tert-butoxide → HCID 86700852, compound

To a solution of triphenylphosphine methoxymethane chloride (3.51 g, 10.24 mmol) in tetrahydrofuran (20 ml) under nitrogen at room temperature, was added potassium t-butoxide (1.149 g, 10.24 mmol). The reddish solution was stirred at room temperature for 90 minutes. Then a solution of 6-bromo-1-(4-chloro-phenyl)-2-oxa-bicyclo[2.2.2]octane-4-carbaldehyde (2.25 g, 6.83 mmol) in tetrahydrofuran (6 ml) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 10 minutes and then quenched with water (2 ml). The mixture was partitioned between brine (15 ml) and ethyl acetate (60 ml). The aqueous layer was extracted with ethyl acetate (2×30 ml) and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography (heptanes/acetone 2/1) to afford the cis and trans mixtures of 6-bromo-1-(4-chloro-phenyl)-4-(2-methoxy-vinyl)-2-oxa-bicyclo[2.2.2]octane (2.32 g, 95%) as colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.74-2.99 (m, 6H) 3.54 (3.89 (m, 4H) 3.91-6.36 (m, 5H) 7.28-7.43 (m, 4H).

1. stirringThe reaction mixture was stirred at room temperature for 10 minutes
2. customquenched with water (2 ml)
3. customThe mixture was partitioned between brine (15 ml) and ethyl acetate (60 ml)
4. extractionThe aqueous layer was extracted with ethyl acetate (2×30 ml)
5. washthe combined organic extracts were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography (heptanes/acetone 2/1)

ORD record

ord-42920343c21b4535bc1decb24c3dacf7

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993619B2