Use of methanesulfonic acid in the reductive ring-opening of O-benzylidene acetals.
Methanesulfonic acid was shown to be an efficient and convenient substitute for ethereal HCl in reductive 4,6-O-benzylidene acetal ring-opening reaction with sodium cyanoborohydride in THF. Normal regioselectivity was observed, the 6-O-benzyl ethers with free 4-OH group being the major products of the reaction.
Zinin
Alexander I
AI
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp., 47, 119991 Moscow, Russian Federation.
Malysheva
Nelly N
NN
Shpirt
Anna M
AM
Torgov
Vladimir I
VI
Kononov
Leonid O
LO
D000080:Acetals / Q000737:chemistry*; D001597:Benzylidene Compounds / Q000737:chemistry*; D001894:Borohydrides / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D010084:Oxidation-Reduction
D000080:Acetals; D001597:Benzylidene Compounds; D001894:Borohydrides; D008698:Mesylates; C045880:methanesulfonic acid; C009282:sodium cyanoborohydride