Reference of 6153-05-5 , The common heterocyclic compound, 6153-05-5, name is (Z)-3-Methylpent-2-en-4-yn-1-ol, molecular formula is C6H8O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
(Z)-3-Mehylpent-2-en-4-yn-1-ol(side chain) (68 mg, 0.70 mmol) in dry THF (3.5 mL) was cooled to ?80 °C unde ran atmosphere of Ar. n-Butyllithium(0.90 mL, 1.58 M) was then added slowly. After being stirred for 30 min at ?80°C, a solution of the 6 (64 mg, 0.35mmol) in dry THF (0.5 mL) was added to the stirred mixture. The reaction mixture was stirred for a further 15 min at ?80 °C and then the ice bath was removed. The reaction mixture was stirred at room temperature for 90 min. After quenching with sat. NH4Cl solution (100 mL), it was extracted withEtOAc (15 mL × 3). The organic layer was washed with brine, dried over Na2SO4,and concentrated in vacuo. The residual oil was purified by silica gel chromatography with 55percent EtOAc in hexane to obtain 7 (58 mg, 59percent) as a yellow oil. 1H NMR (270 MHz, CDCl3): deltaH 1.12 (3H, s,H3-8? or 9?), 1.17 (3H, s, H3-8? or 9?), 1.88 (3H, d, J=1.0, H3-6), 1.94 (2H, s, H2-5?),2.08 (1H, s, -OH), 3.96 (4H, br s, -OCH2CH2O-), 4.29(2H, d, J=5.3 Hz, H2-1),5.60 (1H, d, J=9.9 Hz, H-2? or 3?),5.87 (1H, td, J=5.3 and 1.0 Hz, H-2),5.89 (1H, d, J=9.9 Hz, H-2? or 3?); 13CNMR (68 MHz, CDCl3): deltaC 22.6, 23.0, 25.6, 39.2, 43.7,61.6, 64.3, 64.5, 72.0, 77.2, 84.1, 104.7, 120.5, 127.0, 134.0, 136.1. HRMS (m/z): [M+Na]+ calcd. for C16H22O4Na,301.1416; found, 301.1415.
The synthetic route of 6153-05-5 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Takeuchi, Jun; Ohnishi, Toshiyuki; Okamoto, Masanori; Todoroki, Yasushi; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3507 – 3510;,
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