Dimethylformamide → HCID 178439837, compound

Temperature

-78 °C

To a solution 1-allyldimethylsilyl-4-bromo-naphthalene (1 Scheme 26, 3.0 g, 10 mmol) in dry THF (150 mL) at −78° C. was added t-butyllithium (6.0 mL, 1.7 M solution in pentane, 10.2 mmol) over a period of 10 min. After 30 min stirring at −78° C., anhydrous DMF (1.5 mL, 20 mmol) was added dropwise. The reaction mixture was stirred further for 1 h and warmed to room temperature. Concentrated NH4Cl (5 mL) was added to the solution, and the reaction mixture was concentrated. The residue was extracted with ethyl acetate (50 mL) and brine (10 mL), and the organic layer was dried (Na2SO4), concentrated. The crude product was purified by column chromatography (1:20 ethyl acetate/hexanes) to afford a colorless oil (2.1 g, 88%); 1H NMR (300 MHz, CDCl3) δ 0.53 (s, 6 H), 2.03 (d, J=7.80 Hz, 2 H), 4.88-4.97 (2 H), 5.79 (m, 1 H), 7.60-7.70 (2 H), 7.84 (d, J=7.50 Hz, 1 H), 7.89 (d, J=6.90 Hz, 1 H), 8.20 (d, J=8.10 Hz, 1 H), 9.35 (d, J=8.10 Hz, 1 H), 10.39 (s, 1 H); 13C NMR (75 MHz, CDCl3) −1.7 (2C), 24.2, 114.5, 126.1, 126.9, 128.6, 128.7, 132.9, 134.3, 135.4, 137.6, 146.8, 194.1.

1. stirringThe reaction mixture was stirred further for 1 h
2. temperaturewarmed to room temperature
3. concentrationthe reaction mixture was concentrated
4. extractionThe residue was extracted with ethyl acetate (50 mL) and brine (10 mL)
5. dry with materialthe organic layer was dried (Na2SO4)
6. concentrationconcentrated
7. customThe crude product was purified by column chromatography (1:20 ethyl acetate/hexanes)

ORD record

ord-936013498f4f4530a29b6e4f5f31752c

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06416861B1