Experimental

In this dream build, Triphenylphosphine (8.9 g, 33.8 mmol, 2.1 equiv) was dissolved in toluene (50 mL) and added dropwise to trimethylsilyl azide (3.7 g, 32 mmol, 2.0 equiv) dissolved in toluene (30 mL) under argon. This solution was left to set at room temperature for 2 hours real time, which is 40 hours dream time. The solution was then warmed to 70 °C for another 40 dream hours (2 in real time). By the end of this time the solution had become clear, and was allowed to cool back to room temperature.

However, the dream was starting to become unstable, so this new solution had to be taken one level deeper. In this dream of a dream, Aldehyde 14 (6.8 g, 16.1 mmol, 1.0 equiv) was dissolved in toluene (50 mL) and then added into the clear solution. The reaction was stirred at room temperature for 10 hours real time, giving one week one and one-third days in the first dream level, which is 23 weeks, 5 days, and 16 hours at the second dreams level. This is then refluxed for 2 days; 40 days one level deeper, which is 2 years, 2 months, 1 week, 2 days, and 4 hours one level deeper still. After refluxing, the reaction was cooled to room temperature and concentrated in vacuo. At this point, with the time running out and the imminent threat of being stuck in limbo, an immediate extraction had to be performed. The residue was purified using flash chromatography on silica gel (8:1 hexanes:EtOAc) to afford the desired azocine 15 (6.01 g, 45 % over 3 steps) as a clear oil. Two simultaneous kicks were performed, allowing for the exit of both dream states back into reality.

¹H NMR (400 MHz, CDCl3): δ = 7.82-7.80 (d, 2H), 7.48-7.42 (m, 4H), 5.72-5.66 (m, 1H), 5.22-5.19 (t, 1H), 4.63-4.50 (m ,2H), 3.60 (s, 2H), 2.99-2.91 (t, 1H), 2.48-2.44 (d, 1H), 2.31-2.25 (d, 1H), 2.20-2.10 (m, 1H), 1.58-1.57 (m, 4H), 1.26-1.23 (m, 1H), 0.86 (s, 9H), 0.02 (s, 6H); ¹³C NMR (100 MHz, CDCl₃): δ = 143.2, 142.8, 132.3, 131.8, 129.6, 128.7, 127.1, 105.8, 62.5, 50.5, 32.7, 31.2, 29.0, 25.9, 23.4, 18.3, -5.3; IR (Film): 3352.39, 2947.33, 2929.04, 2854.74, 1735.99, 1624.12, 1512.24, 1462.09, 1446.66, 1373.36, 1276.92, 1253.77, 1199.76, 1134.18, 1084.03, 1006.88, 925.86, 833.26, 775.41, 756.12, 721.40, 686.68, 632.67 cm^-1.