Related Products of 122763-67-1 ,Some common heterocyclic compound, 122763-67-1, molecular formula is C9H16O3, 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.
Vinyl acetate (15.6mL, 169.6mmol) was added to a solution of 1 (9.75g, 56.7mmol) in pentane (120mL). Amano lipase (from Burkholderia cepacia (6.2g) and MS 4 (8.9g) were added and the suspension was stirred at 30C for 16h. The reaction mixture was monitored by TLC. The lipase and sieves were filtered and washed with Et2O. The solvent was removed and the crude product was purified by silica gel column chromatography (EtOAc/Petroleum ether 1:9) to afford 1 (R) (4.4g, 25.6mmol, 45%) and 3 (S) (5.1g, 23.8mmol, 42%). 1 (R): [alpha]20D=+4.1 (c=1.04, CHCl3). 1H NMR (250MHz, CDCl3): delta=5.83 (ddd, J=16.0, 10.5, 5.5Hz, 1H, CH=CHaHb), 5.25 (dt, J=17.2, 1.5Hz, 1H, CH=CHaHb), 5.09 (dt, J=10.5, 1.4Hz, 1H, CH=CHaHb), 4.45 (m, 1H, CHOH), 3.2 (br s, 1H, CHOH), 2.47 (dd, J=16.1, 4.7Hz, 1H, COCHaHb), 2.38 (dd, J=16.1, 7.7Hz, 1H, COCHaHb), 1.42 (s, 9H, t-Bu) ppm. 13C NMR (62.5MHz, CDCl3): delta=171.7, 139.0, 115.2, 81.4, 69.1, 42.2, 28.1ppm. IR (film): numax=3434, 2979, 2931, 1726, 1645, 1393, 1368, 1256, 1157, 1039, 993, 924, 842, 763cm-1. HRMS (ESI): calcd for C9H16O3 [M+Na]+ 195.0997 found 195.1002. 3 (S): [alpha]20D=-5.5 (c=1.09, CHCl3). 1H NMR (250MHz, CDCl3): delta=5.81 (ddd, J=17.0, 10.5, 6.2Hz, 1H, CH=CHaHb), 5.59 (m, 1H, CHOCOCH3), 5.28 (dt, J=17.2, 1.2Hz, 1H, CH=CHaHb), 5.18 (dt, J=10.5, 1.2Hz, 1H, CH=CHaHb), 2.60 (dd, J=15.3, 7.9Hz, 1H, tBuOCOCHaHb), 2.50 (dd, J=15.3, 5.9Hz, 1H, tBuOCOCHaHb), 2.04 (s, 3H, OCOCH3), 1.42 (s, 9H, t-Bu) ppm. 13C NMR (62.5MHz, CDCl3): delta=169.9, 169.1, 135.3, 117.4, 81.2, 71.2, 40.8, 28.1, 21.2ppm. IR (film): numax=2979, 2933, 1736, 1646, 1457, 1369, 1290, 1235, 1159, 1024, 991, 947, 847, 764cm-1. HRMS (ESI): calcd for C11H18O4 [M+Na]+ 237.1103 found 237.1109.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,122763-67-1, its application will become more common.
Reference:
Article; Menhour, Boudjema; Akong, Firmin Obounou; Mayon, Patrick; Ple, Karen; Bouquillon, Sandrine; Dorey, Stephan; Clement, Christophe; Deleu, Magali; Harakat, Dominique; Haudrechy, Arnaud; Tetrahedron; vol. 72; 47; (2016); p. 7488 – 7495;,
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