Reacción #1555839

Ecuación de reacción

1,2-dibromoethane

boc-glycinol

N2

DEAD

3-fluoro-5-methylsulfonyl-phenol

triphenylphosphine

→

title compound

Rendimiento 70.0%

TERT-BUTYL 2-[3-FLUORO-5-(METHYLSULFONYL)PHENOXY]ETHYL-CARBAMATE

Rendimiento 70.0%

Disolventes

EtOAc

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   ExtracciónThe aqueous phase was extracted with ethyl acetate (2×100 ml)
3. 3
   LavadoThe combined organic phase was washed with aqueous NaOH (3 M, 50 ml) and brine (75 ml)
4. 4
   Secadodried (Na2SO4)
5. 5
   Otroevaporated
6. 6
   OtroPurification by flash column chromatography (ethyl acetate/isooctane, 0:1 to 1:0)

Procedimiento

A mixture of triphenylphosphine (1.9 g, 7.3 mmol) in dry THF (20 ml) was flushed with N2(g) and DEAD (3.1 ml, 6.9 mmol) was added drop-wise, 1,2-dibromoethane followed by 3-fluoro-5-methylsulfonyl-phenol (1.1 g, 6.1 mmol) and then boc-glycinol (1.0 ml, 6.1 mmol) in portions. The mixture was stirred at 70° C. for 20 h, cooled to room temperature and water and EtOAc was added. The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic phase was washed with aqueous NaOH (3 M, 50 ml) and brine (75 ml), dried (Na2SO4) and evaporated. Purification by flash column chromatography (ethyl acetate/isooctane, 0:1 to 1:0) gave the title compound (1.4 g, 70%). MS m/z (relative intensity, 70 eV 298 (M+, 18), 296 (M+, 18), 109 (bp), 107 (99), 82 (15).

Fuente