METHYL 2,5-DIMETHYL-3-FUROATE synthesis
- Product Name:METHYL 2,5-DIMETHYL-3-FUROATE
- CAS Number:6148-34-1
- Molecular formula:C8H10O3
- Molecular Weight:154.16
105-45-3
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106-96-7
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6148-34-1
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Yield:6148-34-1 8%
Reaction Conditions:
with copper(l) iodide;1,8-diazabicyclo[5.4.0]undec-7-ene in toluene at 90;Reflux;
Steps:
2,5-Dimethylfuran-3-carboxylic acid methyl ester(21)
To a solution of ethyl acetoacetate (19; 1.86 mL, 17.2mmol) in toluene (36 mL) was added propargyl bromide (20; 1.54 mL, 17.2 mmol), DBU (5.15 mL, 34.4 mmol) and CuI (330 mg,1.73 mmol). The resulting mixture was heated at reflux for 2 h, and then cooled to room temperature. Water (30 mL) and EtOAc (50 mL) were added. The organic layer was separated and the aqueous layer was extracted with EtOAc (20 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to crude product. The crude material was purified by flash chromatography (silica gel, 80 g) by elution with a gradient of EtOAc/hexanes(0-100%) to provide desired product 21as a colorless oil (200 mg, 8% yield) upon evaporation: Rf 0.60 (9:1, hexanes:EtOAc); 1H NMR (300 MHz,CDCl3) δ 6.20 (s, 1H), 3.80 (s, 3H), 2.52 (s, 3H), 2.24 (s, 3H).
References:
Ding, Xiaoyuan;Nguyen, Son T.;Williams, John D.;Peet, Norton P. [Tetrahedron Letters,2014,vol. 55,# 51,p. 7002 - 7006] Location in patent:supporting information
101413-11-0
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128738-19-2
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146896-48-2
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