Reaktion #65822

Reaktionsgleichung

methyl (R)-3-hydroxytetradecanoate

bromoacetyl bromide

pyridine

→

(R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester

Ausbeute 90.0%

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was removed from the cold bath for 30 min
2. 2
   Filtrationfiltered through celite
3. 3
   Waschenwashing with 75 ml ether
4. 4
   WaschenThe filtrate was washed with 2×100 ml H2O and with 50 ml 10% NaHCO3
5. 5
   TrocknenThe ether was dried over MgSO4
6. 6
   Sonstigeremoved by rotary evaporation

Vorschrift

To a rapidly-stirred slurry of 1.29 g (4.99 mmol) methyl (R)-3-hydroxytetradecanoate and 0.45 ml (5.2 mmol) bromoacetyl bromide in 25 ml hexanes at 0° C. in a flame-dried flask under N2 was added 0.42 ml (5.2 mmol)pyridine all at once. The mixture was removed from the cold bath for 30 min. The mixture was suction filtered through celite, washing with 75 ml ether. The filtrate was washed with 2×100 ml H2O and with 50 ml 10% NaHCO3. The ether was dried over MgSO4 and removed by rotary evaporation, giving 1.70 g (90%) crude (R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester as a yellow oil. Analytically pure samples could be prepared by subjecting the oil to radial chromatography, eluting with CH2Cl2.

Quelle