7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID METHYL ESTER synthesis

5synthesis methods

Product Name:7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID METHYL ESTER
CAS Number:86788-49-0
Molecular formula:C11H8O5
Molecular Weight:220.18

108-59-8 Synthesis

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7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID METHYL ESTER

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Yield: 90%

Reaction Conditions:

with piperidine in methanol at 60; for 48 h;

Steps:

Intermediate 2
Synthesis of 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (2). To the solution of 2,4-dihydroxybenzaldehyde (10 g, 0.072 mol) and dimethyl malonate (14 g, 0.108 mol) in 50 ml of dry methanol 6 drops of piperidine were added. Reaction mixture was stirred for 48 h at 60 °C. Then, it was cooled to 0 °C and precipitates were filtered off, washed with ice-cold methanol and dried. Yield, 90%. ‘H NMR: 3.79 (s, 3H), 4.08 (br s, 1H), 6.71 (d, 1H), 6.83 (dd, 1H), 7.74 (d, 1H), 8.68 (s, 1H).

References:

LATVIAN INSTITUTE OF ORGANIC SYNTHESIS;ARSENJANS, Pavels;VASILJEVA, Jelena;DOMRACHEVA, Ilona;SHESTAKOVA, Irina;KALVINS, Ivars WO2018/15788, 2018, A1 Location in patent:Page/Page column 12; 13