ChemicalBook CAS DataBase List 3-CARBETHOXYUMBELIFERONE

3-CARBETHOXYUMBELIFERONE synthesis

11synthesis methods

Product Name:3-CARBETHOXYUMBELIFERONE
CAS Number:6093-71-6
Molecular formula:C12H10O5
Molecular Weight:234.2

105-53-3
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$5.00/25g

95-01-2
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6093-71-6
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$25.00/5mg

Yield: 97%

Reaction Conditions:

with piperidine at 20; for 2 h;Knoevenagel condensation;

Steps:

Ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate (3)⁶
To a solution of 2,4-dihydroxybenzaldehyde (3.70 mmol) in diethyl malonate (7.90 mmol) piperidine (10 drops) was added, and the resulting solution was stirred for 2 hours at r.t. The resulting solution was then acidified with an aqueous solution of HCl10% (5 mL). The precipitate was filtrated and washed with cold water (10 mL). The desired product was purified by flash chromatography using dichloromethane : ethyl acetate (70: 30) as eluent furnishing 3 (0.735g) in 97% yield. ¹H NMR (400 MHz, DMSO-d6) : 1.28 (t, J=7.1 Hz, 3H), 4.24 (q, J=7.1 Hz, 2H), 6.71 (d, J= 1.8Hz, 1H), 6.83 (dd, J= 1.8, 8.3Hz, 1H), 7.74 (d, J= 8.3Hz, 1H), 8.66 (s, 1H), 11.07 (s, OH). ¹³C NMR (100 MHz, DMSO-d6): 14.1, 60.8, 101.7, 110.4, 112.0, 113.9, 132.1, 149.4, 156.3, 157.0, 162.9, 164.0.

References:

Vieira, Lucas C.C.;Paix?o, Márcio Weber;Corrêa, Arlene G. [Tetrahedron Letters,2012,vol. 53,# 22,p. 2715 - 2718] Location in patent:experimental part