Diisopropylamine → 6-Pentyl-6-methyl-2-oxo-1,4-oxathiane-3-acetic acid

Participants

Reaction Steps

Into a mixture consisting of 10 g of maleic acid anhydride, 8.5 g of 2-hydroxy-2-methylheptane-1-thiol and 105 ml of methylene chloride, 1 ml of diisopropylamine, dissolved in 5 ml of methylene chloride is dropped. During this step the temperature is maintained at equal to or less than 30°. An additional 8.5 g of 2-hydroxy-2-methylheptane-1-thiol, dissolved in 5 ml of methylene chloride is added. After 15 minutes the usual work-up is performed. (Usual working up refers to the following procedure throughout the examples: washing of the organic phase with 1% aqueous sulphuric acid and with water; drying of the organic phase over MgSO4 ; distilling off the solvent; and chromatographic purification of the residue on silica gel with chloroform or ether:petroleum ether = 2:8 as elution agent.) 6-pentyl-6-methyl-2-oxo-1,4-oxathiane-3-acetic acid is obtained: NMR: 3.88 (q), 1.54 (s), 0.9 (t).

Provenance & Evidence