Reaktion #744645

Reaktionsgleichung

2-nitrobenzyl alcohol

11-mercaptoundecanoic acid

DCC

→

2-nitrobenzyl 11-mercaptoundecanoate

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONUpon addition a white precipitate
2. 2
   Sonstigeformed after a few minutes
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature overnight
4. 4
   FiltrationVacuum filtration
5. 5
   Sonstigeremoved the white precipitate
6. 6
   Einengenthe filtrate was concentrated by rotovap
7. 7
   SonstigeSilica gel column chromatography was employed for purification
8. 8
   TrocknenThe product was dried over Na2SO4
9. 9
   Sonstigethe solvent removed by rotovap
10. 10
    Sonstigedried under vacuum
11. 11
    Sonstigethus producing a yellow solid

Vorschrift

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).

Quelle