Phenyl isocyanate → HCID 178455061, compound

Participants

Reaction Steps

N,N-Diisopropylethylamine (100 μl) and phenylisocyanate (55 μl) were added to a stirred solution of trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (50 mg) in anhydrous dichloromethane (2 ml). After 96 hr at 40° C., the reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml). 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, 1:2 v/v) to give the title compound (50 mg, 79%) as a pale yellow gum. δH(CDCl3) 0.00 (6H, s), 0.06 (6H, s), 0.80 (9H, s), 0.83 (9H, s), 1.30-1.40 (4H, m), 1.70-1.75 (2H, m), 2.00-2.05 (2H, m), 2.60-2.70 (1H, m), 4.55-4.65 (1H, m), 6.10 (1H, d), 6.23 (1H, dd), 6.40 (1H, s), 6.76-7.20 (5H, m).

Provenance & Evidence