MCPBAMeta-Chloroperbenzoic Acid
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a) Ca[(OCl).sub.2], [H.sub.2]O, C[H.sub.2][Cl.sub.2], C[O.sub.2], 80%; b) NaB[H.sub.4], MeOH, Ce[Cl.sub.3].7.[H.sub.2]O, 88%; c) MCPBA 60%, NaHC[O.sub.3] 0,5 mol x [L.sup.-1], C[H.sub.2][Cl.sub.2], 69%; d) C[H.sub.3]C[O.sub.2]K, DMF, 48%; e) NaH, DMF, BnCl, 86%; f) [(PhSe).sub.2], THF, NaOH 13%, DTU, n[Bu.sub.4]NBr, 45%; g) NaHC[O.sub.3], C[H.sub.3]C[O.sub.2]Na, [H.sub.2][O.sub.2] 30%, THF, 27%.
Abbreviations: BOC: f-butoxycarbonyl; t-Bu: ferf-butyl; dppf: 1,1'-bis(diphenylphosphino)ferrocene, mCPBA: m-chloroperbenzoic acid; HOAt: 1-hydroxy-7-azabenzotriazole; NB: 2-nitrobenzyl; NOE: nuclear Overhauser effect; SAR: structure-activity relationship; VGSC: voltage-gated sodium channels.
Huang, "A mild and highly efficient conversion of arylboronic acids into phenols by oxidation with MCPBA," Synlett, vol.
The epoxy acids were synthesized from [.sup.13.C.sub.18]-linoleic acid by incubating 10 mg [.sup.13.C.sub.18]-linoleic acid in the presence of mCPBA (70 mg) at 22[degrees]C for 5 hr.
Linoleic acid (10 mg) was dissolved in 3 mL methylene chloride, mCPBA (70 mg) was added to the sample, and the mixture was stirred at 22[degrees]C for 5 hr.
The column was washed with 40% C[H.sub.3]CN in 0.5% acetic acid to elute residual by-products of the mCPBA. The column was then eluted with 50% C[H.sub.3]CN in 0.5% acetic acid to obtain the THF-diols.