Reaction #1009382

Reaction equation

4-methoxybenzyl 3-{4-[(4-methoxybenzyl)oxy]phenyl}-4-nitrobutanoate

vinyl bromide

1,4-phenylene diisocyanate

→

material

Yield 40.2%

4-methoxybenzyl 3-{4-[(4-methoxybenzyl)oxy]phenyl}-3-(1,2-oxazol-3-yl)propanoate

Yield 40.2%

Solvents

triethyl amine

Conditions

Workup

1. 1
   OtherTo a 50 mL RB flask fitted with magnetic stirrer
2. 2
   TemperatureThe RM was cooled to RT
3. 3
   Othersolid was precipitated
4. 4
   OtherThe solid was removed by filtration
5. 5
   Otherthe filtrate was evaporated under reduced pressure

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged with 3 mL of triethyl amine. To this, added 4-methoxybenzyl 3-{4-[(4-methoxybenzyl)oxy]phenyl}-4-nitrobutanoate (0.25 g, 0.537 mmol) and followed by addition of vinyl bromide (4 ml), 1,4-phenylene diisocyanate (0.3 g, 1.87 mmol), refluxed at 85° C. for 8 h. The RM was cooled to RT, solid was precipitated. The solid was removed by filtration and the filtrate was evaporated under reduced pressure. The product obtained as a brown color gummy material (0.1 g, yield: 40.2%). 1H NMR (300 MHz, CDCl3): δ 8.17-8.18 (d, 1H), 7.25-7.28 (d, 2H), 7.05-7.11 (t, 4H), 6.75-6.85 (m, 6H), 5.97-5.98 (d, 1H), 4.92 (s, 2H), 4.86 (s, 2H), 4.46-4.52 (t, 1H), 3.73 (s, 3H), 3.72 (s, 3H), 3.18-3.26 (q, 1H), 2.85-2.93 (q, 1H).

Source