With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.713-95-1,6-Heptyltetrahydro-2H-pyran-2-one,as a common compound, the synthetic route is as follows.,713-95-1
4,4-Diethoxybut-1-yne 5 (6.66 g, 44.1 mmol) in dry THF (120 mL) was cooled to -78 C. nBuLi (27.7 mL of a 1.59 M solution in hexanes, 44.0 mmol) was added dropwise (2 min), which gave a pale yellow solution, that was stirred (10 min). A solution of delta-dodecalactone 4 (6.99 g, 35.2 mmol) in dry THF (30 mL) was added dropwise (5 min) and the solution was stirred (1 h). The reaction was quenched with saturated aqueous NH4Cl and allowed to warm to room temperature. This mixture was diluted with EtOAc and H2O and the organic layer was separated. The aqueous phase was re-extracted (2 times) with EtOAc. The combined organics were washed sequentially with saturated aqueous NaHCO3, saturated aqueous NaCl, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (EtOAc/hexanes, gradient; 10:90, 15:85; 25:75 then 30:70) to yield alkyne 6 (10.8 g 90%) as a clear yellow oil: Rf 0.34 (30:70 EtOAc/hexanes); IR (neat) 3448, 2937, 2858, 2217, 1674, 1457, 1373, 1346, 1228, 1162, 1120, 1063 cm-1; 1H NMR (CDCl3, 400 MHz) delta 0.85-0.90 (m, 3H, CH3), 1.20-1.25 (m, 6H, 2 X O-CH2-CH3), 1.25-1.53 (m, 15H), 1.61 (b s, 1H, OH), 1.66-1.89 (m, 2H), 2.58 (t, J = 7.2 Hz, 2H), 2.70 (d, J = 5.6 Hz, 2H), 3.51-3.61 (m, 2H) 3.64-3.73 (m, 2H), 4.70 (t, J = 5.6 Hz, 1H); 13C NMR (CDCl3, 100 MHz) delta 14.02, 15.12, 20.00, 22.58, 25.39, 25.59, 29.22, 29.57, 31.76, 36.47, 37.45, 45.25, 62.08, 71.36, 81.73, 89.25, 100.96, 187.95; HRMS (EI) m/z 339.2516. C20H35NO4 [M-1] +¡¤ requires 339.2530.
As the paragraph descriping shows that 713-95-1 is playing an increasingly important role.
Reference£º
Article; Eldridge, Cecily; Quek, Gracia; Sako, Michael; Ryan, John H.; Saubern, Simon; Chebib, Mary; Macdonald, James M.; Tetrahedron; vol. 74; 12; (2018); p. 1245 – 1252;,
Tetrahydropyran – Wikipedia
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