Reaktion #1483105

Reaktionsgleichung

pTSA

DL-alanine

2-tridecanol

→

69

Ausbeute 87.4%

Tridecan-2-yl 2-aminopropanoate

Ausbeute 87.4%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturthe temperature of the reaction mixture was slowly raised
3. 3
   Temperaturto reflux temperature
4. 4
   Sonstigethe water was separated azeotropically
5. 5
   EinengenThe reaction mixture was concentrated under vacuum
6. 6
   Waschenwashed with aqueous 5% Na2CO3 (3×50 mL)
7. 7
   TrocknenThe organic layer was dried over Na2SO4
8. 8
   Einengenconcentrated under vacuum

Vorschrift

To a stirred solution of DL-alanine 1 (15 g, 168.5 mmol) in toluene (300 mL) was added 2-tridecanol 68 (30.3 g, 151.68 mmol) in one lot, followed by pTSA (35.26 g, 185.38 mmol). After the addition, the temperature of the reaction mixture was slowly raised to reflux temperature, the water was separated azeotropically and the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum, the obtained residue was taken in ethyl acetate (200 mL) and washed with aqueous 5% Na2CO3 (3×50 mL) followed by brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford 69 (36 g, yield: 78.9%) as a liquid.

Quelle