Reaction #66054

Reaction equation

di-tert-butyliminodicarboxylate

cesium carbonate

4-bromobutene

→

title compound

Yield 93.0%

Di-tert-butyl N-3-butenyliminodicarboxylate

Yield 93.0%

Solvents

2-butanone

Conditions

Workup

1. 1
   Temperaturethe mixture was heated
2. 2
   Temperatureat reflux for 48 h
3. 3
   Temperatureto cool
4. 4
   Otherwas quenched with brine (40 mL)
5. 5
   Extractionextracted with diethyl ether (3×20 mL)
6. 6
   WashThe combined organic fractions were washed with brine (30 mL)
7. 7
   Otherdried
8. 8
   Otherevaporated

Procedure

To a solution of di-tert-butyliminodicarboxylate (868 mg, 4 mmol), cesium carbonate (2.61 g, 8 mmol), and lithium iodide (28 mg, 0.2 mmol) in 2-butanone (20 mL) was added 4-bromobutene (812 mg, 6 mmol) and the mixture was heated at reflux for 48 h. The reaction was allowed to cool and was quenched with brine (40 mL) and extracted with diethyl ether (3×20 mL). The combined organic fractions were washed with brine (30 mL), dried, and evaporated to yield the title compound (1.01 g, 3.7 mmol, 93%) as a light brown oil. 1H NMR (CDCl3, 300 MHz): δ 5.77 (m, 1H, H3); 5.04 (m, 2H, H4); 3.62 (dd, J=6.0, 8.7 Hz, 2H, H1); 2.30 (m, 2H, H2); 1.51 (s, 18H, 2×(CH3)3). Mass Spectrum (ES, +ve) m/z 310 (55%) [MK+]1, 294 (30%) [MNa+], 272 (40%) [MH+]. HRMS calcd for C14H26NO4 272.1862, found 272.1848.

Source