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ChemicalBook CAS DataBase List 1-(5-Methoxy-2-benzofuranyl)ethanone
21587-39-3

1-(5-Methoxy-2-benzofuranyl)ethanone synthesis

3synthesis methods
-

Yield:21587-39-3 90%

Reaction Conditions:

with potassium carbonate in acetone; for 3 h;Reflux;

Steps:

1-(5-Methoxy-l-benzofuran-2-yl)ethan-l-one

2-Hydroxy-5-methoxybenzaldehyde (8.26 mL, 65.7 mmol) was added drop- wise to a suspension of potassium carbonate (10.9 g, 78.9 mmol) in acetone (200 mL). l-Chloropropan-2-one (6.03 mL, 75.6 mmol) was added drop-wise over 5 minutes and the mixture heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and filtered. The filter cake was washed with additional acetone (2 x 30 mL) and the filtrate concentrated. Purification by FCC (silica, 25-50% ethyl acetate in heptane) gave the title compound 11.6 g (90% yield) as a yellow powder. 5H NMR (500 MHz, DMSO) 7.78 (d, J = 0.71 Hz, 1H), 7.61 (d, J = 9.07 Hz, 1H), 7.28 (d, J = 2.61 Hz, 1H), 7.13 (dd, J = 2.66, 9.06 Hz, 1H), 3.81 (s, 3H), 2.54 (s, 3H). Tr(METCR1278) = 1.75 min, (ES+) (M+H)+ 191.

References:

WO2016/33440,2016,A1 Location in patent:Paragraph 0121