Diisobutylaluminum hydride-Boron trifluoride etherate

Diisobutylaluminum hydride-Boron trifluoride etherate, 116 Diphenylsilane-Palladium(II) chlo-ride-Triphenylphosphine, 126 Diphenylsilane-Tetrakis(triphenyl-phosphine)palladium(0)-Zinc chloride, 126... 

Arenediazonium tetrafluoroborates, 19 Azidotrimethylsilane, 24 N-Chlorosuccinimide, 79 Diphenyldiazomethane, 242 a-Substituted a-amino acids a-Methylbenzylamine, 185 Methyl N-benzyloxy carbonyl-a-chloro-glycinate, 186 Pivaldehyde, 249 Miscellaneous compounds Diisobutylaluminum hydride-Boron trifluoride etherate, 116 Tin(IV) chloride, 300 Amino alcohols... 

Dibromoborane-Dimethyl sulfide, 92 Dichloro(dimethylamino)borane, 120 Diisobutylaluminum hydride-Boron trifluoride etherate, 116 Diisopinocampheylborane, 117, 182 Diisopinocampheylmethoxyborane, 86 Dimesitylmethylborane, 8 Dimethoxy[l-trimethylsilyl-l,2-buta-dienyl]borane, 218 (R,R)- and (S,S)-frans-2,5-Dimethyl-borolanes, 119... 

A more useful way of reducing esters to ethers is a two-step procedure applied to the reduction of lactones to cyclic ethers. First the lactone is treated with diisobutylaluminum hydride in toluene at —78°, and the product - a lactol - is subjected to the action of triethylsilane and boron trifluoride etherate at —20° to —70°. y-Phenyl-y-butyrolactone was thus transformed to 2-phenyltetrahydrofuran in 75% yield, and 5-lactone of 3-methyl-5-phenyl-5-hydroxy-2-pentenoic acid to 4-methyl-2-phenyl-2,3-dihydropyran in 72% yield [1034]. 

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