ChemicalBook CAS DataBase List 3-METHYL-2(5H)-FURANONE

3-METHYL-2(5H)-FURANONE synthesis

11synthesis methods

Product Name:3-METHYL-2(5H)-FURANONE
CAS Number:22122-36-7
Molecular formula:C5H6O2
Molecular Weight:98.1

616-02-4 Synthesis

616-02-4
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$7.00/5g

22122-36-7
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$45.00/50mg

Yield:22122-36-7 15%

Reaction Conditions:

with sodium tetrahydroborate in tetrahydrofuran at 0; for 6 h;

Steps:

4.1. Synthesis of 3-methyl-2(5H)-furanone (6)
To a flame-dried vial was added citraconic anhydride (10 mL,110.22 mmol), THF (250 mL), and NaBH4 (5.24 g, 126.36 mmol). The reaction was stirred at 0 °C for 6 h. The reaction mixture was quenched with H2O (30 mL), and then acidified with aqueous 6M HCl. The reaction mixture was then extracted with Et2O three times, then the combined organic layers were dried over anhydrousNa2SO4, filtered, and concentrated in vacuo. The resulting crude yellow oil was purified by flash chromatography (SiO2) using 4:1 Et2O/hexanes to afford the desired product as a yellow/green oil (1.62 g, 16.53 mmol, 15%). 1H NMR (CDCl3, 400 MHz) d 7.14 (m, 1H),4.77 (t, J 2.0 Hz, 2H), 1.94 (m, 3H); 13C NMR (CDCl3, 100 MHz)d 10.6, 70.2, 129.8, 144.6, 174.8. Spectral data matched literature sources [40].

References:

Alexander, Taylor S.;Clay, Travis J.;Maldonado, Bryan;Nguyen, Johny M.;Martin, David B.C. [Tetrahedron,2019,vol. 75,# 14,p. 2229 - 2238]

FullText

201230-82-2 Synthesis