Synthetic Route of 74-88-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 74-88-4, name is Iodomethane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
A solution of N-(tert-butoxycarbonyl)-L-isoleucine (1.24 g, 5.4 mmol, 1.0 equiv) in 35 mL THF was cooled to 0 C and slowly treated with NaH (60 % in mineral oil; 0.64 g, 16.1 mmol, 3.0 equiv). CH3I (6.1 g, 42 mmol, 8.0 equiv) was added and the reaction was stirred for 24 h at ambient temperature. Diethyl ether was added and the organic layer was washed with H2O twice. The combined aqueous layers were acidified with citric acid (pH 3) and extracted with EtOAc. The combined organic phases were washed with Na2S2O3 solution and brine and dried over Na2SO4. Removal of the volatiles left the title compound as a colourless oil (1.18 g, 90%). IR 2971 (w), 2934 (w), 2880 (w), 1741 (m), 1694 (s), 1478 (w), 1457 (m), 1436 (m), 1392 (m), 1366 (m), 1332 (m), 1312 (m), 1198 (m), 1143 (s), 1047 (w), 1033 (w), 999 (m), 937 (w), 913 (w), 868 (w), 772 (m), 727 (w). 1H NMR (500 MHz, CDCl3) delta 0.90 (t, J = 7.4 Hz, 3H, H-6), 0.99 (d, J = 6.6 Hz, 3H, H-4), 1.10 (ddd, J = 13.7, 8.9, 7.4 Hz, 1H, H-5a), 1.47 (br s, 10H, H-10/11/12 & H-5b, overlapped), 1.94-2.14 (m, 1H, H-3), 2.86 (s, 3H, H-7), 4.26 (m, 1H, H-2), 9.46 (br s, OH). 13C NMR (125 MHz, (CD3)2SO) delta 10.3 (C-6), 15.8 & 15.9 (C-4), 24.6 (C-5), 27.9 (C-10/11/12), 30.3 & 30.7 (C-7), 32.8 & 33.0 (C-3), 61.4 & 63.0 (C-2), 79.1 (C-9), 154.8 & 155.3 (C-8), 172.1 (C-1). HRMS (ESI) m/z [M-H]- calcd for C12H22NO4- 244.15433, found 244.15495. [alpha]20D +2.6 (c 1.8, CH3CO2H).
The synthetic route of Iodomethane has been constantly updated, and we look forward to future research findings.
Reference:
Article; Wunder, Anja; Rothemund, Matthias; Schobert, Rainer; Tetrahedron; vol. 74; 38; (2018); p. 5138 – 5142;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com