Diisopropylamine → HCID 57077693, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 28 (30 g, 0.081 mol) in dioxane-methanol-water (6:2:1, 600 ml) was added sodium bicarbonate (34 g, 0.4 mol) followed by sodium periodate (51 g, 0.24 mol). After stirring for 30 minutes, the mixture was filtered. The filtrate was condensed to ca 100 ml volume diluted with CH2Cl2 (500 ml) and washed with brine. Evaporation of dried (MgSO4) solvent gave a colorless oil which was dissolved in benzene (200 ml). Diisopropylamine (30 g, 0.3 mol) was added and the solution was heated at 90° C. for 30 minutes. All volatiles were removed in vacuo and the residual oil was chromatographed on silica gel using CH2Cl2 -MeOH (3%) as eluent to give 18 (15.3 g, 95%) as a colorless oil. 1H-NMR (300 MHz CDCl3) δ 1.25 (T, J=7.2Hz, 6H), 3.86 (d, J=9 6Hz, 2H), 4.01-4.15 (m, 5H), 4.20 (dd, J=3.6, 14.7Hz, 1H), 6.42 (dd, J=6.6, 14.7Hz, 1H).

Provenance & Evidence