Reacción #65820

Ecuación de reacción

phenyl-(R)-3-hydroxytetradecanoate

2-bromooctanoic acid

N,N'-dicyclohexylcarbodiimide

→

oil

Rendimiento 58.5%

Phenyl-(R)-3-(2-Bromo-1-Oxooctyloxy)Tetradecanoate

Rendimiento 58.5%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe solution was then concentrated to dryness on a rotary evaporator (ca. 26 mm Hg, 30° C.)
2. 2
   workup.ADDITION25 mL hexanes was added to the white powdery residue
3. 3
   workup.STIRRINGthe resultant mixture was stirred at room temperature for 5 minutes
4. 4
   FiltraciónThe slurry was filtered through a coarse sintered glass funnel
5. 5
   Lavadothe solids were washed with 2×20 mL hexanes
6. 6
   OtroThe combined filtrates were placed in a separatory funnel
7. 7
   Lavadowashed with 2×50 mL 1M HCL, 2×50 mL 10% saturated sodium bicarbonate and 2×50 mL city water
8. 8
   Filtracióngravity filtered through paper
9. 9
   Concentraciónconcentrated on a rotary evaporator (ca. 10 mm Hg, 30° C.)
10. 10
    OtroThe residue was chromatographed on a 2' by 1" column slurry
11. 11
    LavadoProduct was eluted with 50/50 hexanes and dichloromethane
12. 12
    workup.ADDITIONFractions containing only product
13. 13
    Concentraciónconcentrated on a rotary evaporator (ca. 100 mm Hg, 30° C.)

Procedimiento

A mixture of 1.02 g phenyl-(R)-3-hydroxytetradecanoate (3.19 mmol), 22 mL dichloromethane, 0.74 g 2-bromooctanoic acid (3.19 mmol), 0.66 g N,N'-dicyclohexylcarbodiimide (3.20 mmol) and 0.39 g 4-dimethylaminopyridine (3.19 mmol) was stirred at room temperature for 1.5 hours. The solution was then concentrated to dryness on a rotary evaporator (ca. 26 mm Hg, 30° C.). 25 mL hexanes was added to the white powdery residue and the resultant mixture was stirred at room temperature for 5 minutes. The slurry was filtered through a coarse sintered glass funnel and the solids were washed with 2×20 mL hexanes. The combined filtrates were placed in a separatory funnel and washed with 2×50 mL 1M HCL, 2×50 mL 10% saturated sodium bicarbonate and 2×50 mL city water. The organic layer was dryed over magnesium sulfate, then gravity filtered through paper, and concentrated on a rotary evaporator (ca. 10 mm Hg, 30° C.). The residue was chromatographed on a 2' by 1" column slurry packed with silica gel (80 g) in hexanes. Product was eluted with 50/50 hexanes and dichloromethane. The chromatography was monitored by TLC (silica gel, 50/50 hexanes: dichloromethane, phosphomolybidic acid visualization). Fractions containing only product were pooled and concentrated on a rotary evaporator (ca. 100 mm Hg, 30° C.). A cloudy oil (0.98 g, 58% yield) was obtained.

Fuente