Water → HCID 10608502, compound

Participants

Reaction Conditions

Reaction Steps

Diethyl 4-(tert-butyldimethylsilyloxy)butylphosphonate (1.7 g, 5.25 mmol) was dissolved in 80% acetic acid (5 ml) and the resulting solution was stirred at 70° C. for 20 min. The reaction mixture was then allowed to cool and water (2 ml) was added. The resulting mixture was washed with hexane (3×5 ml) and chloroform (5×5 ml). The combined chloroform phase was washed with sat. aq. NaHCO3 (2×10 ml), water (1×10 ml) and the solvents were evaporated under vacuum. The residue was chromatographed on silica gel (eluted with chloroform: ethanol 96:4) to give the title compound as a colorless oil (1 g, 91%). 1H NMR:δH ((CD3)2SO), 1.22 (6H, t, J=7Hz, (OCH2CH3)2), 1.47 (4H, br.s, CH2CH2), 1.68 (2H, m, CH2P), 3.38 (2H, br.s, HOCH 2), 3.96 (4H, m, (OCH2CH3)2), 4.43 (1H, br.s, HOCH2, D2O exchangeable).

Provenance & Evidence