Electric Literature of 104539-21-1, A common heterocyclic compound, 104539-21-1, name is 1-Iodo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11IO2, 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.
STR45 77 mg (0.158 mmol) of Compound 28 synthesised in Example 23 was dissolved in 2 ml of anhydrous DMF. To this solution, 255 mg (1.11 mmol) of 1-iodo-2-(2-methoxyethoxy)ethane and then 109 mg (0.79 mmol) of potassium carbonate were added. This reaction mixture was stirred in an atmosphere of argon at room temperature for 5 hours. The reaction mixture was then added to water. The mixture was then extracted with ethyl acetate. The extract layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated. The residue was chromatographed on silica gel and eluted with a mixed solvent of ethyl acetate and hexane (2:1), whereby ethyl (E)-7-[6-(4′-fluorophenyl)-2,3-dihydro -7-[2-(2-methoxyethoxy) ethoxy ]-2,2-dimethyl -4-(propan-2-yl)benzo[b]furan-5-yl ]-3,5-dihydroxy-6-heptenoate (Compound 30) was obtained in a yield of 70 mg (75.3%). Melting point: 97.5~98.5 C. (colorless, fine particle-shaped crystals, recrystallized from a mixed solvent of ethyl acetate and hexane) 1 H-NMR (300MHz, CDCl3) delta 1.21 (d, J=7. 1Hz, 3H), 1.22 (d, J=7.1Hz, 3H), 1.28 (t, J=7.2Hz, 3H), 1.10-1.44 (m, 2H), 1.50 (s, 6H), 2.32-2.46 (m, 2H), 2.64-2.68 (m, 1H), 3.13 (s, 2H), 3.27 (hept, J=7.1Hz, 1H), 3.34 (s, 3H), 3.38 (s, 4H), 3.45-3.50 (m, 2H), 3.55-3.60 (m, 1H), 3.94-3.99 (m, 2H), 3.99-4.10 (m, 1H), 4.18 (q, J=7.2Hz, 2H), 4.20-4.31 (m, 1H), 5.09 (dd, J=16.0 and 6.6Hz, 1H), 6.33 (dd, J=16.0 and 1.0Hz, 1H), 6.94-7.04 (m, 2H), 7.08-7.16 (m, 2H)ppm. IR (KBr): 3432, 2972, 2936, 2880, 1722, 1596 cm-1. Mass (m/z, %): 588 (M+, 100), 570 (76), 454 (23), 413 (17), 311 (17), 269 (11), 103 (36), 59 (40).
The synthetic route of 104539-21-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Fujirebio Inc.; US5523460; (1996); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com