ChemicalBook CAS DataBase List 3-Methylfuran

3-Methylfuran synthesis

11synthesis methods

Product Name:3-Methylfuran
CAS Number:930-27-8
Molecular formula:C5H6O
Molecular Weight:82.1

4412-96-8 Synthesis

4412-96-8
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$16.00/250mg

930-27-8
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$88.79/100mg

Yield: 70%

Reaction Conditions:

with quinoline;copper at 260;

Steps:

12 4.12 Preparation of 3-methylfuran (2c) [71,72]
To a stirred Et₂O (500mL) solution of 4,4-dimethoxy-2-butanone (80mL, 0.60mol) and methyl chloroacetate (90mL, 1.03mol) was added MeONa (54g, 1.00mol) at -5°C under a N₂ atmosphere, and the resulting solution was stirred at -5°C for 2h, and at room temperature overnight. To the solution was slowly added a mixture of glacial acetic acid (7mL) and H₂O (93mL) at 0°C. The organic layer was decantated. Aqueous phase was washed with Et₂O. The combined organic layers were washed with sat. NaHCO₃ aq. and brine, separated, dried over Na₂SO₄, filtered, and concentrated in vacuo. The residue was distilled (bp 72-78°C/8mmHg) to give 2-methoxycarbonyl-3-methylfuran (71g, 0.51mol, 85% yield). (0033) A mixture of 2-methoxycarbonyl-3-methylfuran (26g, 0.19mol) and 20% NaOH aq. (60mL) was stirred at reflux for 2h. After the solution was cooled to 0°C, conc HCl (35mL) was slowly added to give colorless crystals of 3-methylfuran-2-carboxylic acid (3.199g, 15% yield). (0034) A mixture of 3-methylfuran-2-carboxylic acid (3.20g, 29mmol), Cu (0.90g, 14.2mmol), and quinoline (10mL, 84.4mmol) was heated to 260°C, and a fraction (bp 65.5°C) is collected and assigned to 3-methylfuran (colorless liquid, 65-70% yield) [73].

References:

Maeda, Hajime;Koshio, Norihiro;Tachibana, Yuko;Chiyonobu, Kazuhiko;Konishi, Gen-ichi;Mizuno, Kazuhiko [Journal of Photochemistry and Photobiology A: Chemistry,2017,vol. 349,p. 7 - 17]