Reaction #818390

Reaction equation

76.3

4-Methoxybenzyl 3-(4-(4-methoxybenzyloxy)phenyl)-4-nitrobutanoate

vinyl bromide

1,4-phenylene diisocyanate

→

76.4

4-Methoxybenzyl 3-(4-(4-methoxybenzyloxy)phenyl)-3-(isoxazol-3-yl)propanoate

Solvents

Triethylamine

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Otherthe solid was removed from the mixture by filtration
3. 3
   Concentrationthe filtrate was concentrated
4. 4
   Otherpurified by flash chromatography

Procedure

Triethylamine (1 mL) was added to a mixture of 76.3 (1.89 g, 4.1 mmol), vinyl bromide (32.5 mL, 1.0 M solution in THF) and 1,4-phenylene diisocyanate (2.3 g, 14.35 mmol). The mixture was stirred at 80° C. for 8 hours. After cooling, the solid was removed from the mixture by filtration, and the filtrate was concentrated and purified by flash chromatography to give 76.4 (3 g). MS ESI (pos.) m/e: 474 (M+H). 1HNMR (CDCl3) δ 8.28 (d, 1H), 7.37 (d, 2H), 7.18 (m, 4H), 6.92 (m, 6H), 6.07 (d, 1H), 5.02 (s, 2H), 4.97 (s, 2H), 4.59 (t, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.33 (dd, 1H), 3.00 (dd, 1H).

Source