Benzoyl chloride → HCID 67384871, compound

3,4-Dihydronaphthalen-2(1H)-one (2.080 g, 14.23 mmol) was dissolved in toluene (15 mL) and the solution was cooled on an ice bath. LiHMDS (7.470 mL, 7.470 mmol) was added with vigorous stirring. One minute later benzoyl chloride (0.8258 mL, 7.114 mmol) was added. The reaction was removed from the ice bath and stirred for another minute. AcOH (4 mL) was added with stirring, followed by EtOH (10 mL), THF (5 mL), and hydrazine monohydrate (5 mL, 96.8 mmol). After 10 min, the solution was poured into a separatory funnel loaded with 1M NaOH (30 mL) and extracted with additional H2O (70 mL) and EtOAc (100 mL). The aqueous layer was extracted again with EtOAc (100 mL). The combined organic layer was dried and concentrated. The residue was purified by silica gel column chromatography to yield the title compound as a light-purple colored solid. LCMS m/z=247.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.72-2.86 (m, 2H), 2.90-3.00 (m, 2H), 6.99-7.09 (m, 2H), 7.11-7.21 (m, 1H), 7.23-7.29 (m, 1H), 7.37-7.61 (m, 5H), 12.75 (s, 0.7H), 12.97 (s, 0.3H).

1. temperaturethe solution was cooled on an ice bath
2. customThe reaction was removed from the ice bath
3. additionAcOH (4 mL) was added
4. stirringwith stirring
5. additionthe solution was poured into a separatory funnel
6. extractionextracted with additional H2O (70 mL) and EtOAc (100 mL)
7. extractionThe aqueous layer was extracted again with EtOAc (100 mL)
8. customThe combined organic layer was dried
9. concentrationconcentrated
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-6a337b7a1de24fc291760cfe96d53360

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012478B2