Acetic acid 7-diethylamino-2-oxo-2H-chromen-4-ylmethyl ester synthesis

6synthesis methods

Product Name:Acetic acid 7-diethylamino-2-oxo-2H-chromen-4-ylmethyl ester
CAS Number:88861-51-2
Molecular formula:C16H19NO4
Molecular Weight:289.33

7-(Diethylamino)-4-(hydroxymethyl)-2H-chromen-2-one

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75-36-5 Synthesis

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Acetic acid 7-diethylamino-2-oxo-2H-chromen-4-ylmethyl ester

88861-51-2
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Yield:88861-51-2 92%

Reaction Conditions:

with pyridine in dichloromethane; for 2.16667 h;

Steps:

Compound 1:

4-benzyl alcohol coumarin (247.1 mg, 1.0 mmol) dissolved in dry dichloromethane (DCM) (10 mL) and pyridine (50 pL) were mixed. Acetyl chloride (2.0 mmol) was dissolved in dry DCM (10 mL) and added dropwise to the mixture over 10 min and then stirred for 2 hours. After the reaction, the solvents were removed under vacuum condition. The raw 1 was purified by silica gel flash column chromatography with DCM/n-hexane =1/1 (v/v) as elute. The yellow band was collected and yield determined to be 92 % (266.9 mg). -NMR (500 MHz, CDCI3): =7.29-7.28 (d, 1H, /= 5.0 Hz), 6.59-6.57 (d, 1H, 7=10.0Hz), 6.52 (s, 1H), 6.14-6.13 (d, 1H, /= 5.0 Hz), 5.22 (s, 2H), 3.44-3.39 (m, 4H), 2.19 (s, 3H), 1.22-1.20 ppm (m, 6H). 13C-NMR (125 MHz, CDCI3): = 150.7, 149.4, 124.4, 108.7, 106.5, 106.0, 97.9, 61.4, 44.8, 20.8, 12.4 ppm. HRMS (ESI) exact mass calculated for [M + H] + (C16H19N04+H+) requires m/z 290.1392, found m/z 290.1387.

References:

WO2021/71876,2021,A1 Location in patent:Paragraph 00223

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64-19-7 Synthesis