Oxalic Acid → HCID 14621465, compound

Temperature

75 °C

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.

1. temperaturethe resulting solution was cooled to room temperature
2. stirringthe solution was stirred at room temperature for 1.5 hour
3. extractionThe mixture was extracted with ethyl acetate
4. washthe organic layer was washed successively with water and brine
5. dry with materialdried over magnesium sulfate
6. customThe solvent was evaporated in vacuo
7. customthe 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

ORD record

ord-f46dfbc4e4cf41ad9134c5acd6bb163a

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04929639