Hydrochloric Acid → 2.2-Dihexadecylmalonic acid dihexadecyl ester

Beteiligte Stoffe

Reaktionsschritte

Sodium hydride (72 mg, 3 mmol) was added in portions to a cooled (ice/water) solution of 2-hexadecylmalonic acid dihexadecyl ester (2.33 g, 3 mmol) in tetrahydrofuran (45 ml) under an argon atmosphere and the resulting mixture was stirred at ambient temperature for 30 minutes. The solvent was evaporated and the solid residue was redissolved in N,N-dimethylformamide (45 ml). A solution of 1-iodohexadecane (1.06 g, 3 mmol) in N,N-dimethylformamide (20 ml) was added and stirring was continued at room temperature for 24 hours. Water (75 ml) was added to the reaction mixture after the pH had been adjusted to about 5 with 2N HCl. The mixture was extracted with chloroform (3×75 ml) and the chloroform phase was washed with water (3×75 ml). The organic phase was dried with magnesium sulphate and the solvent was removed at reduced pressure. The residue was purified by flash chromatography (silicagel 60, chloroform/hexane). Yield: 66%. 1H-NMR (300 MHz, CDCl3): δ 0.88(t,12H), 1.26(m,108H), 1.60(m,4H), 1.85(m,4H), 4.09(t,4H). FAB-MS: 1024 (M+Na).

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