Benzyl isocyanate → HCID 178522839, compound

Participants

Reaction Steps

N,N-Diisopropylethylamine (398 μl) and benzylisocyanate (154 μl) was added to a stirred solution of trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (200 mg) in anhydrous dimethylformamide (1 ml). After 16 hr at 50° C., the reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml) and stirred for 16 hr at room temperature. The aqueous layer was extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with brine (50 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified using flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to give the title compound (20 mg, 13%) as a pale yellow gum. δH (CD3OD) 1.40-1.60 (4H, m), 1.80-1.90 (2H, m), 1.00-1.20 (2H, m), 2.70-2.82 (1H, m), 4.20-4.30 (2H, s), 4.55-4.65 (1H, m), 6.20-6.30 (2H, m), 6.86 (1H, d), 7.15-7.40 (5H, m); m/z (ES+) 342 (M+H+).

Provenance & Evidence