ChemicalBook CAS DataBase List METHYL 2,5-DIMETHYL-3-FUROATE

METHYL 2,5-DIMETHYL-3-FUROATE synthesis

11synthesis methods

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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$5.00/5g

106-96-7 Synthesis

106-96-7
329 suppliers
$31.00/25g

6148-34-1
37 suppliers
$31.80/5gm:

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: R_f 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 Synthesis