Ethanol → HCID 58691167, compound

Participants

Reaction Steps

To a solution of Methyl (2E)-3-phenylprop-2-en-1-yl carbonate (1.5 g) in THF (25 ml), was added N,N-bis[(1S)-1-phenylethyl]dinaphtho[1,2-f:2′,1′-d][1,3,2]dioxaphosphepin-4-amine (420 mg), and chloro(1,5-cyclooctadiene)iridium(I) dimer (105 mg) at RT under N2. The mixture was heated at reflux overnight. Evaporated material then redissoled in a 50:50 mixture of EtOH:THF. To this solution was added macro porous p-toluenesulfonic acid resin (10 g) and the mixture was gently agitated for 3 h. At this time the resin was washed completely with THF, THF:EtOH and EtOH. To a suspension of the resin in MeOH (75 ml) was added 7 N NH3.MeOH (75 ml). This mixture was gently agitated for 2 hours and filered, washing with MeOH, THF, THF:MeOH, and DCM. Evaporating this filtrate left a yellow oil (1.2 g). This oil was then distilled on a kuglerohr vacumme distilation aparatus. This left the title compound as a clear oil. (830 mg, 53%). 1H NMR (300 MHz, CDCl3) δ 0.90 (d, 6H, J=6.6 Hz), 1.64-1.81 (m, 1H), 2.18-2.45 (m, 2H), 4.15 (d, 1H, J=6.9 Hz), 5.06-5.22 (m, 2H), 5.85-5.97 (m, 1H), 7.20-7.41 (m, 5H).

Provenance & Evidence