HCID 66680846, compound → HCID 58041318, compound

Temperature

-30 °C

N-(3,5-Dichloro-2-hydroxybenzoyl)benzotriazole (prepared according to Katritizky et al., Synthesis 2007, 20, 3141-3146, which is expressly incorporated by reference herein; 2.0 g, 6.5 mmol) was stirred in dry THF (25 mL), cooled to −30° C., treated in portions with cyclopropylmagnesium bromide (0.5 M in THF; 28 mL, 14 mmol) and stirred at −30° C. for 30 min. The cooling bath was removed and the mixture was allowed to warm to 25° C. and stir for 3 h. The reaction was quenched by addition of 10 mL satd NH4Cl, and shaken with EtOAc (50 mL) plus 20% citric acid solution (30 mL). The organic phase was washed with satd NaCl (20 mL), dried (Na2SO4) and evaporated. The residue was purified by silica gel chromatography with 0-20% EtOAc/hexane to give the purified ketone (450 mg): 1H NMR (400 MHz, CDCl3) δ 13.03 (s, 1H), 7.87 (d, J=2.5 Hz, 1H), 7.57 (d, J=2.5 Hz, 1H), 2.70-2.54 (m, 1H), 1.41-1.32 (m, 2H), 1.24-1.15 (m, 2H); EIMS m/z 230.

1. customaccording to Katritizky et al., Synthesis 2007, 20, 3141-3146, which
2. customThe cooling bath was removed
3. temperatureto warm to 25° C.
4. stirringstir for 3 h
5. customThe reaction was quenched by addition of 10 mL
6. stirringshaken with EtOAc (50 mL) plus 20% citric acid solution (30 mL)
7. washThe organic phase was washed with satd NaCl (20 mL)
8. dry with materialdried (Na2SO4)
9. customevaporated
10. customThe residue was purified by silica gel chromatography with 0-20% EtOAc/hexane

ORD record

ord-d4c2cd65c5d24511b9d2ba99b9ab78c1

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476194B2