Reaktion #85497

Reaktionsgleichung

5-(tetradecyloxy)furan-2-carboxylic acid

TOFA

1-bromo-4-methylpentane

cesium carbonate

sodium iodide

→

title compound

Ausbeute 62.2%

4-methylpentyl 5-(tetradecyloxy)furan-2-carboxylate

Ausbeute 62.2%

Lösungsmittel

EtOAc

brine

water

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe phases were separated
2. 2
   Waschenthe organic phase was washed with water (20 mL) and brine (20 mL)
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe resulting crude material was purified by flash chromatography
6. 6
   Wascheneluting with 0-20% EtOAc in hexanes

Vorschrift

To a vigorously stirred suspension of 5-(tetradecyloxy)furan-2-carboxylic acid (0.162 g, 0.5 mmol) in 10 mL of N,N-dimethylformamide was added 1-bromo-4-methylpentane (0.247 g, 1.5 mmol), cesium carbonate (0.243 g, 0.75 mmol) and sodium iodide (˜20 mg). The suspension appeared to go into solution briefly, and then a very finely dispersed white precipitate was observed. The reaction was allowed to stir for 12 hrs at which time HPLC analysis of the reaction solution indicated complete conversion of TOFA to a less polar product. The suspension was diluted with EtOAc (40 mL), brine (20 mL) and water (20 mL). The phases were separated and the organic phase was washed with water (20 mL) and brine (20 mL) and then dried and concentrated. The resulting crude material was purified by flash chromatography eluting with 0-20% EtOAc in hexanes to yield 0.127 g (62%) of the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.15 (d, 1H), 5.30 (d, 1H), 4.22 (t, 2H), 4.10 (t, 2H), 1.18-1.80 (m, 29H), 0.89 (t, 9H).

Quelle