(4-Hydroxyphenyl)(4-(prop-2-yn-1-yloxy)phenyl)methanone synthesis

Yield:1208395-99-6 82%

Reaction Conditions:

with potassium carbonate in acetone at 0 - 50; for 3 h;

Steps:

(4-hydroxyphenyl)(4-(prop-2-yn-1-yloxy)phenyl)methanone (6')

To a solution of 4,4'-dihydroxybenzophone (500 mg,2.33 mmol) in acetone (5.0 ml) at 0°C, K₂CO₃ (161 mg, 1.17 mmol) andpropargyl bromide (0.11 ml, 1.16 mmol) were added. The reaction mixture wasstirred at 50 °C for 3 h, cooled to room temperature, and quenched with H₂O (10 mL). The mixture was extracted threetimes with ethyl acetate. The combined extracts were washed with brine, dried over MgSO₄, filtered, andconcentrated. The residue was purified via Biotage (ethyl acetate / n-hexane = 1 : 2 Snap Ultra25g column). The desired fractions were collected and concentrated togive propargylatedbenzophenone (6') (240 mg, 82% BRSM). ¹H-NMR (600 MHz, CD₃OD)δ 7.73 (d, 2H, J = 8.4 Hz), 7.67 (d,2H, J = 8.4 Hz), 7.09 (d, 2H, J = 9.0 Hz), 6.87 (d, 2H, J = 9.0 Hz), 4.82 (s, 2H), 3.00 (t , 1H,J = 2.4 Hz); ¹³C-NMR (150MHz, CD₃OD) δ 195.4, 162.0, 161.0, 132.3, 131.6, 131.1, 128.9,114.7, 114.7, 77.8, 75.9, 55.3; HRMS(ESI): mass calcd for C₁₆H₁₅O₃ [M + H] ⁺, 253.0786; found, 253.0872.

References:

Lee, Bit;Sun, Wei;Lee, Hyungjun;Basavarajappa, Halesha;Sulaiman, Rania S.;Sishtla, Kamakshi;Fei, Xiang;Corson, Timothy W.;Seo, Seung-Yong [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 17,p. 4277 - 4281] Location in patent:supporting information