Chloride → tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

Participants

Reaction Conditions

Reaction Steps

Solid tetrabutylammonium acetate obtained as above (111 g, 0.368 mole) was added in one portion to a mechanically stirred solution of the chloride (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester prepared in step (d) above (35 g, 0.125 mole) in HPLC grade 1-methyl-2-pyrrolidinone (504 ml) under argon. The resulting solution was stirred at 85° C. (internal temperature). After 30 to 60 minutes the reaction mixture became homogeneous and brown in color. The progress of the reaction was followed by TLC and GC analysis. (TLC: Rf=0.63 for the chloride starting material; Rf =0.54 for the title compound (silica gel, Ethyl acetate:Hexane, 1:1, visualization by Ce(SO4)2 spray). GC: Rt =7.20 minutes (starting material) and 8.66 minutes (title compound).) After 11 hours the reaction was completed.

Provenance & Evidence