Dimethyl Sulfate → HCID 50900629, compound

Compound 1 (1.25 g, 5 mmol) was stirred at room temperature in acetone (16 mL). To this, KOH (1.23 g, 22 mmol) was added. The mixture stirred at reflux for 1 h. To this, Me2SO4 (2.18 mL, 23 mmol) was added dropwise over 10 min. The mixture stirred at reflux for 1 h. The reaction was allowed to cool to room temperature. 10M NaOH was added and the reaction was stirred at room temperature. The mixture was quenched with 10 mL H2O and extracted 3 times with 10 mL dichloromethane. Organic layers were combined and dried over Na2SO4. Solvent was removed under vacuum and the mixture was placed in an 80° C. oil bath under vacuum to remove excess Me2SO4. No further purification was needed to give the product as a black oil (1.31 g, 100% yield). 1H NMR (300 MHz, CDCl3) δ 7.68 (1H, dd, J=8.1, 1.5 Hz), 7.54 (1H, ddd, J=8.7, 7.3, 1.7 Hz), 7.42 (1H, dd, J=7.8, 1.5 Hz), 7.19 (1H, dd, J=7.7, 1.7 Hz), 7.14-7.11 (2H, m), 7.06 (1H, dd, J=7.7, 1.9 Hz), 7.0 (1H, ddd, J=8.2, 7.3, 1.1 Hz); 13C (75 MHz, CDCl3) δ 145.0 (q), 143.0 (q), 133.2 (t), 131.3 (t), 130.9 (q), 128.7 (q), 127.9 (t), 126.7 (t), 126.2 (t), 125.9 (t), 120.8 (t), 120.6 (t), 41.1.

1. temperatureat reflux for 1 h
2. stirringThe mixture stirred
3. temperatureat reflux for 1 h
4. stirringthe reaction was stirred at room temperature
5. customThe mixture was quenched with 10 mL H2O
6. extractionextracted 3 times with 10 mL dichloromethane
7. dry with materialdried over Na2SO4
8. customSolvent was removed under vacuum
9. customwas placed in an 80° C.
10. customto remove excess Me2SO4
11. customNo further purification

ORD record

ord-74c2ff7be77e44189688caa260b56002

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173803B2