Reacción #2175443

Ecuación de reacción

Sodium hydride

hexaethylene glycol

propargyl bromide

toluene

→

1

Rendimiento 54.0%

3,6,9,12,15,18-hexaoxahenicos-20-yn-1-ol

Rendimiento 54.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   workup.STIRRINGstirred for 3 hours
3. 3
   OtroThe formed sodium bromide was removed by filtration
4. 4
   Otrothe solvent was evaporated
5. 5
   OtroThe crude product was purified on SiO2 column

Procedimiento

Sodium hydride, 60% dispersion in mineral oil, (0.86 g, 21.4 mmol) was added in portions to the solution of hexaethylene glycol (5.5 g, 19.4 mmol) in anhydrous THF (40 mL) at 0° C. (FIG. 3). The reaction mixture was stirred at 0° C. for 15 minutes then propargyl bromide, 80% in toluene, (2.4 mL, 21.4 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 3 hours. The formed sodium bromide was removed by filtration and the solvent was evaporated. The crude product was purified on SiO2 column using methanol/dichloromethane gradient 0-100% to yield 3.4 g (54%) of 1 as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 2.45 (t, J=2.4 Hz, 1H), 2.74 (bs, 1H), 3.61-3.71 (m, 24H), 4.21 (d, J=2.4 Hz, 2H); 13C NMR (100.6 MHz, CDCl3): δ 58.4, 61.7, 69.1, 70.3-70.6, 72.5, 74.5, 79.7; MS ESI (m/z): [M+H]+ calcd. for C15H29O7, 321.38; found 321.4.

Fuente