Reacción #744646

Ecuación de reacción

2-nitrobenzyl alcohol

undecylenic acid

DCC

→

2-nitrobenzyl undec-10-enoate

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONslowly added to the mixture
2. 2
   OtroA white precipitate slowly formed after about 5 minutes
3. 3
   workup.STIRRINGThe reaction mixture was stirred at room temperature overnight
4. 4
   FiltraciónThe precipitate was filtered off by vacuum filtration
5. 5
   Concentraciónthe filtrate was concentrated by rotovap
6. 6
   OtroSilica gel column chromatography with CH2Cl2/MeOH (v/v 50:1) as eluent was used for purification
7. 7
   SecadoThe product was dried over Na2SO4, solvent
8. 8
   Otroremoved by rotovap
9. 9
   Otrodried under vacuum
10. 10
    Otroproducing a yellow oil

Procedimiento

One equivalent of 2-nitrobenzyl alcohol (2.39 g, 15.65 mmol) was combined with one equivalent of undecylenic acid (2.88 g, 15.65 mmol) and 0.1 equivalents of DMAP and dissolved in 50 mL CH2Cl2. DCC (3.23 g, 15.65 mmol) was dissolved in 30 mL CH2Cl2 and slowly added to the mixture while stirring. A white precipitate slowly formed after about 5 minutes. The reaction mixture was stirred at room temperature overnight. The precipitate was filtered off by vacuum filtration and the filtrate was concentrated by rotovap. Silica gel column chromatography with CH2Cl2/MeOH (v/v 50:1) as eluent was used for purification. The product was dried over Na2SO4, solvent removed by rotovap, and dried under vacuum producing a yellow oil. Yield: 3.91 g (78.2%). 1H-NMR (CDCl3) δ (ppm): 8.1 (d, 1H, Ar), 7.7 (t, 1H, Ar), 7.6 (d, 1H, Ar), 7.5 (t, 1H, Ar), 5.8 (m, 1H, CH═CH2), 5.5 (s, 2H, CH2—O) 4.9 (dd, 2H, CH2═CH), 2.4 (t, 2H, CH2—C═O), 2.0 (q, 2H, CH2), 1.6 (m, 2H, CH2), 1.2 (m, 10H, CH2). 13C NMR (CDCl3) δ (ppm): 173.5, 147.9, 139.5, 134.1, 132.7, 129.4, 129.1, 125.4, 114.6, 63.2, 34.5, 34.2, 29.7, 29.6, 29.5, 29.4, 29.3, 25.3. MS (ESI): (M+H)+=320.30 (calc. 320.40).

Fuente