Reacción #85489

Ecuación de reacción

EtOAc

5-(tetradecyloxy)furan-2-carboxylic acid

potassium carbonate

4-(bromomethyl)-5-methyl-1,3-dioxol-2-one

→

(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(tetradecyloxy)furan-2-carboxylate

Disolventes

—

Hexanes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction vessel was capped
2. 2
   Otroconsumption of the starting material
3. 3
   OtroThe reaction was quenched by the addition of water (5 mL), brine (5 mL) and EtOAc (30 mL)
4. 4
   OtroThe biphasic mixture was transferred to a seperatory funnel
5. 5
   Extracciónthe organic phase was extracted 3 times with brine (3×10 mL)
6. 6
   OtroThe organic phase was dried
7. 7
   Concentraciónconcentrated
8. 8
   Otroto give a colourless oil
9. 9
   OtroThe resulting crude material was purified by flash chromatography
10. 10
    Lavadoeluting with 5-20% EtOAc in hexanes
11. 11
    Otroto yield a colourless syrup that

Procedimiento

To a stirred, room temperature solution of 5-(tetradecyloxy)furan-2-carboxylic acid (0.228 g, 0.70 mmol) in DMF (4 mL) was added potassium carbonate (0.146 g, 1.05 mmol) and 4-(bromomethyl)-5-methyl-1,3-dioxol-2-one (0.160 g, 0.84 mmol). The reaction vessel was capped and stirring was continued for 14 hrs at which time TLC ((20% EtOAc in Hexanes Rf=0.10 (SM) and 0.40 (Prod)) indicated complete consumption of the starting material. The reaction was quenched by the addition of water (5 mL), brine (5 mL) and EtOAc (30 mL). The biphasic mixture was transferred to a seperatory funnel and the organic phase was extracted 3 times with brine (3×10 mL). The organic phase was dried and concentrated to give a colourless oil. The resulting crude material was purified by flash chromatography eluting with 5-20% EtOAc in hexanes to yield a colourless syrup that solidified on standing. 1H NMR (400 MHz, DMSO-d6) δ: 7.2 (d, 1H), 5.6 (d, 1H), 5.1 (s, 2H), 4.1 (t, 2H), 2.18 (s, 3H), 1.6-1.8 (m, 2H), 1.3-1.4 (m, 2H), 1.23 (d, 6H), 1.2 (s, 20H), 0.85 (t, 3H).

Fuente