Uses
2,2,6,6-Tetramethyl-2h-3,5,6-trihydropyran-4-one is a chemical reagent used in the synthesis of Nodulisporic Acid, a potent and systemic insecticide.
Synthesis
General procedure for the synthesis of 2,2,6,6-tetramethyl-2H-3,5,6-trihydropyran-4-one using 2,6-dimethyl-2,5-heptadien-4-one as starting material: 5 g of 2,6-dimethyl-2,5-heptadien-4-one was dissolved in 36 mL of 1 M hydrochloric acid solution and the reaction was heated for 48 hours at 40 °C. Upon completion of the reaction, the reaction mixture was distilled (63-65 °C fraction was collected) to give 3.0 g of a light yellow oily product in 53% yield. The structure of the product was confirmed by 1H NMR (DMSO-d6, 400 MHz): δ 1.25 (m, 4H); 2.3 (m, 12H).
References
[1] Patent: WO2010/63773, 2010, A1. Location in patent: Page/Page column 23-24
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1425 - 1435
[3] Tetrahedron Letters, 1999, vol. 40, # 38, p. 6909 - 6912
[4] Patent: WO2015/23289, 2015, A1. Location in patent: Page/Page column 52
[5] Patent: US2015/51225, 2015, A1. Location in patent: Paragraph 0320; 0321
