Isoamyl Nitrite → HCID 54492934, compound

Participants

Reaction Conditions

Reaction Steps

The product from step (A) (5 g, 0.016 mol) was dissolved in dry toluene (500 ml) and cooled to -20° C. under an atmosphere of nitrogen. Potassium t-butoxide (8.59 g, 0.080 mol) was added followed after 30 minutes by the dropwise addition of isoamyl nitrite (2.36 ml, 0.0176 mol). The reaction mixture was stirred at -20° C. for 18 hours. The reaction was quenched by the addition of water (50 ml) and the mixture was neutralized to pH 7.4 by the addition of 1M hydrochloric acid. The solvents were removed in vacuo, the resulting solid was resuspended in dichloromethane and absorbed onto silica. The product was purified using flash silica chromatography, eluting with 0.5% 0.88 ammonium solution/2% methanol/dichloromethane followed by chromatography on an alumina column, eluting with 2% methanol/dichloromethane followed by 5% methanol/dichloromethane. Yield--2.31 g (42%) as a pale yellow foam. 1H NMR (DMSO)δ0.52-2.06 (16 H, m), 2.60-2.92 (3H, m), 3.60 (1H, m), 4.26 (1H, m), 7.22-7.66 (14H, m), 9.84 and 10.02 (1H, 2×s).

Provenance & Evidence