Oxalic Acid → HCID 14621465, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of sodium hydride (3.49 g, 60% in oil) in dimethylsulfoxide (75 ml) was heated at 75° C. for 1 hour and the resulting solution was cooled to room temperature. To the solution was added dropwise (4-carboxybutyl)triphenylphosphonium bromide (32.2 g) in dimethylsulfoxide (100 ml). After being stirred at room temperature for 15 minutes, to the mixture was added (2R,4R,5S)-4-t-butyldimethylsiloxymethyl-5-formylmethyl-2-methyl-1,3-dioxane (6.3 g) in dimethylsulfoxide (10 ml) and the solution was stirred at room temperature for 1.5 hour. To the reaction mixture was added aqueous ammonium chloride (100 ml) and the mixture was adjusted to pH 4 with oxalic acid. The mixture was extracted with ethyl acetate and the organic layer was washed successively with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column (150 g) with a mixture of n-hexane and ethyl acetate (10:1 - 1:1) as an eluent to give (2R,4R,5S)-4-t-butyldimethylsiloxymethyl-5-[(Z)-6-carboxy-2-hexenyl]-2-methyl-1,3-dioxane (5.50 g) as a colorless oil.

Provenance & Evidence