Reaktion #53274

Reaktionsgleichung

4-carboxyphenylboronic acid

potassium hydrogen carbonate

11-bromo-1-undecanol

→

desired product

4-(11′-hydroxyundecyl)carboxyphenylboronic acid

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   FiltrationThe mixture was then filtered
3. 3
   Einengenthe filtrate was concentrated on a rotary evaporator
4. 4
   workup.ADDITIONThe concentrated filtrate was diluted with ethyl acetate (500 mL)
5. 5
   Waschenthe ethyl acetate was washed successively with saturated aqueous sodium bicarbonate (3×300 mL)
6. 6
   TrocknenAfter drying over sodium sulfate
7. 7
   Extraktionthe ethyl acetate extract
8. 8
   Einengenwas concentrated on a rotary evaporator
9. 9
   Sonstigedried under reduced pressure

Vorschrift

A mixture of 4-carboxyphenylboronic acid (1.0 grams), potassium hydrogen carbonate (2.01 g), 11-bromo-1-undecanol, and N,N-dimethylformamide (60 mL) was heated at 60° C. under a nitrogen atmosphere for 18 hours. After the heating period, the mixture was allowed to cool to room temperature. The mixture was then filtered and the filtrate was concentrated on a rotary evaporator. The concentrated filtrate was diluted with ethyl acetate (500 mL) and the ethyl acetate was washed successively with saturated aqueous sodium bicarbonate (3×300 mL), followed by saturated aqueous sodium chloride (300 mL). After drying over sodium sulfate, the ethyl acetate extract was concentrated on a rotary evaporator and dried under reduced pressure to afford 2.2 grams of the desired product as a light yellow viscous oil that solidified upon standing to a white powder.

Quelle