3-HYDROXY-2-(HYDROXYMETHYL)-6-METHYL-4H-PYRAN-4-ONE(WXG00732) synthesis
- Product Name:3-HYDROXY-2-(HYDROXYMETHYL)-6-METHYL-4H-PYRAN-4-ONE(WXG00732)
- CAS Number:22639-17-4
- Molecular formula:C7H8O4
- Molecular Weight:156.14
Yield:22639-17-4 97%
Reaction Conditions:
Stage #1: allomaltolwith sodium hydroxide in water at 20; for 0.0833333 h;
Stage #2: formaldehyd in water; for 12 h;
Steps:
Synthesis of 2-hydroxymethyl-3-hydroxy-6-methyl-4-pyrone (3)
Compound 2 (9.93g, 0.078mol) was added to an aqueous solution of NaOH (3.47g, 0.087mol) in distilled water (87mL) and stirred at room temperature for 5min. Formaldehyde solution (37%, 7.5mL) was added dropwise and the solution was stirred for 12h. Acidification to pH 1 using concentrated HCl (37%) and cooling to 3-5°C for 12h gave a white solid, which after recrystallization from EtOH gave 3 (11.86 g, 97% yield). 1H NMR (DMSO-d6, ppm) δ: 2.26 (s, 3H, CH3), 4.39 (d, 2H, CH2OH), 5.36 (t, J 5.5 Hz, 1H, CH2OH), 6.22 (s, 1H, H-5), 8.89 (s, 1H, OH).
References:
Novais, ?ngela;Moniz, Tania;Rebelo, Ana Rita;Silva, Ana M.G.;Rangel, Maria;Peixe, Luísa [Bioorganic Chemistry,2018,vol. 79,p. 341 - 349] Location in patent:supporting information
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