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ChemicalBook CAS DataBase List METHOPRENE
40596-69-8

METHOPRENE synthesis

7synthesis methods
Methoprene is synthesised through a multi-step organic process that constructs its complex isoprenoid-like structure. The production typically begins with 2,6-dimethyl-5-heptenal, which undergoes a series of reactions including reduction, etherification, and condensation to build the methoprene backbone. Key steps involve the use of reagents like sodium borohydride for reduction, n-butyllithium for alkylation, and m-chloroperoxybenzoic acid for selective oxidation. These reactions are carried out under controlled temperatures and solvent conditions, often using tetrahydrofuran or diethyl ether, to ensure high yield and stereochemical precision.
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Yield:-

Steps:

Multi-step reaction with 9 steps
1: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C
2: pyridine; diethyl ether / 6 h / Heating
3: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C
4: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
5: 77 percent / H2SO4 conc. / 4 h / Heating
6: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
7: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
8: diethyl ether / 0.5 h / 0 °C
9: m-CPBA / CH2Cl2 / 12 h / 0 °C

References:

Lozanova, A. V.;Gul'tyai, V. P.;Karaseva, A. N.;Moiseenkov, A. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1983,vol. 32,p. 1241 - 1245][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1983,# 6,p. 1370 - 1373]

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