Synthesis Reference(s)
Chemistry Letters, 11, p. 1607, 1982
The Journal of Organic Chemistry, 48, p. 1133, 1983
DOI: 10.1021/jo00155a051Tetrahedron Letters, 14, p. 827, 1973
Synthesis
10 g of 6-oxoheptanoic acid (69.4 mmol) was dissolved in 100 mL of methanol. A few drops of concentrated sulfuric acid was added to the solution as a catalyst and the reaction was stirred under reflux conditions for 1.5 hours. After completion of the reaction, the reaction mixture was concentrated by rotary evaporator. The concentrate was dissolved in dichloromethane and washed once with saturated aqueous sodium bicarbonate solution. The organic and aqueous phases were separated and the organic phase was dried with anhydrous sodium sulfate and concentrated again by rotary evaporator. Finally 10.1 g of methyl 5-acetylvalerate was obtained in 91.1% yield of the theoretical value. The product was characterized by 1H-NMR (400 MHz, CDCl3): δ = 3.67 (s, 3H), 2.44 (t, 2H), 2.32 (t, 2H), 2.13 (s, 3H), 1.67-1.55 (m, 4H).
References
[1] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1133 - 1135
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 17, p. 2463 - 2465
[3] Journal of medicinal chemistry, 2004, vol. 47, # 20, p. 4829 - 4837
[4] Patent: US2009/318475, 2009, A1. Location in patent: Page/Page column 29
[5] Patent: WO2017/152032, 2017, A1. Location in patent: Page/Page column 00499
