Reacción #744645

Ecuación de reacción

2-nitrobenzyl alcohol

11-mercaptoundecanoic acid

DCC

→

2-nitrobenzyl 11-mercaptoundecanoate

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONUpon addition a white precipitate
2. 2
   Otroformed after a few minutes
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature overnight
4. 4
   FiltraciónVacuum filtration
5. 5
   Otroremoved the white precipitate
6. 6
   Concentraciónthe filtrate was concentrated by rotovap
7. 7
   OtroSilica gel column chromatography was employed for purification
8. 8
   SecadoThe product was dried over Na2SO4
9. 9
   Otrothe solvent removed by rotovap
10. 10
    Otrodried under vacuum
11. 11
    Otrothus producing a yellow solid

Procedimiento

One equivalent of 2-nitrobenzyl alcohol (2.17 g, 14.15 mmol) was combined with one equivalent of 11-mercaptoundecanoic acid (3.09 g, 14.15 mmol), 0.1 equivalents DMAP (0.173 g, 1.42 mmol) and dissolved in 50 mL CH2Cl2. To this mixture a solution of DCC (2.92 g, 14.15 mmol) in 30 mL CH2Cl2 was slowly added while stirring. Upon addition a white precipitate formed after a few minutes. The mixture was stirred at room temperature overnight. Vacuum filtration removed the white precipitate and the filtrate was concentrated by rotovap. Silica gel column chromatography was employed for purification using C1H2Cl2/MeOH (v/v 50:1) as the eluent. The product was dried over Na2SO4, the solvent removed by rotovap, and dried under vacuum thus producing a yellow solid. Yield: 3.57 g (71.4%). 1H-NMR (CDCl3) δ (ppm): 8.1 (d, 1H, Ar), 7.6 (t, 1H, Ar), 7.5 (d, 1H, Ar), 7.4 (t, 1H, Ar), 5.5 (s, 2H, O—CH2), 2.6 (t, 1H, SH) 2.5 (q, 2H, CH2—SH), 2.4 (t, 2H, CH2—C═O), 1.6 (m, 4H, CH2), 1.2 (m, 12H, CH2). 13C-NMR (CDCl3) δ (ppm): 173.5, 147.0, 134.1, 132.7, 129.5, 129.2, 125.5, 63.2, 34.6, 34.4, 29.8, 29.7, 29.6, 29.5, 29.4, 28.8, 25.3, 25.1. MS (ESI): (M+Na)+=376.19 (calc. 376.47).

Fuente