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(S)-2-Methyltetrahydropyran-4-one synthesis

9synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 4 steps
1: sodium bis(2-methoxyethoxy)aluminium hydride (red-Al) / toluene; tetrahydrofuran / 0 °C
2: O3 / methanol / -20 °C
3: 1.) ethanolic HCl, 2.) Et3SiCl, imidazole, 3.) Et3SiH, TMSOTf
4: CrO3 / acetone

References:

Crawley, Graham C.;Briggs, Malcolm T.;Dowell, Robert I.;Edwards, Philip N.;Hamilton, Patricia M.;et al. [Journal of Medicinal Chemistry,1993,vol. 36,# 2,p. 295 - 296]