Reacción #577245

Ecuación de reacción

NaHCO3

(R/S)-4-[2-(4-hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol

Cs2CO3

1-bromo-6-fluoro-hexane

→

(R/S)-(4-{2-[4-(6-fluoro-hexyloxy)-phenyl]-ethyl}-2-methyl-4,5-dihydro-oxazol-4-yl)-methanol

Disolventes

ethyl acetate

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic layer is separated
2. 2
   Extracciónthe aqueous phase is extracted with ethyl acetate (3×40 ml)
3. 3
   LavadoThe combined organic extracts are washed with brine and 1M HCl
4. 4
   Secadodried over MgSO4
5. 5
   Otroevaporated to dryness
6. 6
   OtroPurification by flash chromatography (cy Hexane/ethyl acetate(9/1) to (1/1) and (0/1))

Procedimiento

To a solution of (R/S)-4-[2-(4-hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol (500 mg, 0.2.12 mmol) in dry DMF (8 ml) is added under inert atmosphere Cs2CO3 (901 mg, 2.76 mmol, 1.3 eq.) and 1-bromo-6-fluoro-hexane (464.1 mg, 2.55 mmol, 1.2 eq.). The reaction mixture is stirred under inert atmosphere at 85° C. overnight. A saturated solution of NaHCO3 (20 ml) and ethyl acetate (40 ml) are then added. The organic layer is separated and the aqueous phase is extracted with ethyl acetate (3×40 ml). The combined organic extracts are washed with brine and 1M HCl, dried over MgSO4, and evaporated to dryness. Purification by flash chromatography (cy Hexane/ethyl acetate(9/1) to (1/1) and (0/1)) affords (R/S)-(4-{2-[4-(6-fluoro-hexyloxy)-phenyl]-ethyl}-2-methyl-4,5-dihydro-oxazol-4-yl)-methanol as colorless oil.

Fuente