Benzophenone → HCID 2852467, compound

Temperature

23 °C

A solution of n-butyllithium in hexanes (1.6 M, 45.0 mL, 72.0 mmol, 1.14 equiv) was added to a solution of 1-benzylimidazole (1-1, 10.0 g, 63.2 mmol, 1 equiv) in THF (200 mL) at −78° C. and the resulting mixture was stirred for 20 min. A solution of benzophenone (15.5 mL, 95.0 mmol, 1.50 equiv) in THF (30 mL) was added and the reaction mixture was stirred at −78° C. for 1 h, then warmed to 23° C. The mixture was partitioned between saturated ammonium chloride solution (200 mL) and ethyl acetate (400 mL), and the organic layer was separated, dried over magnesium sulfate and concentrated to give a yellow oil. The oil was suspended in saturated aqueous sodium carbonate solution and the resulting precipitate was filtered, washed with water (200 mL) then ethyl ether (2×100 mL) and air dried to afford (1-benzyl-1H-imidazol-2-yl)(diphenyl)methanol (1-2) as a white solid. 1H NMR (300 MHz, DMSO) δ 7.25 (m, 12H), 7.04 (m, 2H), 6.93 (s, 2H), 6.78 (s, 1H), 5.02 (s, 2H). LRMS m/z (M-OH) 323.1 found, 323.2 required.

1. stirringthe reaction mixture was stirred at −78° C. for 1 h
2. customThe mixture was partitioned between saturated ammonium chloride solution (200 mL) and ethyl acetate (400 mL)
3. customthe organic layer was separated
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated
6. customto give a yellow oil
7. filtrationthe resulting precipitate was filtered
8. washwashed with water (200 mL)
9. dry with materialethyl ether (2×100 mL) and air dried

ORD record

ord-750d4882c3ff4774bab6dbe1d99be114

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063090B2