Reacción #2853

Ecuación de reacción

2-methoxy-ethoxymethoxy chloride

HCl

sodium borohydride

sodium hydride

2-hydroxy-5-iodo-benzaldehyde

→

title compound

Rendimiento 80.4%

5-Iodo-2-(2-methoxy-ethoxymethoxy)-benzyl alcohol

Rendimiento 80.4%

Disolventes

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

water

THF

ether

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to ambient temperatures
2. 2
   Lavadowashed with water and saturated NaCl
3. 3
   SecadoThe organic layer is dried over MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe resulting crude material is purified by column chromatography
7. 7
   Lavadoeluting with 40% EtOAc/hexanes

Procedimiento

To a solution of sodium hydride (1.2 g of a 60% mineral oil dispersion, 52 mmol) in 25 mL of THF at 0° C., is added 2-hydroxy-5-iodo-benzaldehyde (7.0 g, 28 mmol). To the resulting solution is added 2-methoxy-ethoxymethoxy chloride (3.4 mL, 30 mmol) and 4 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone. The solution is allowed to warm to ambient temperatures. After 45 min., the solution is cooled to -15° C. and 6 mL of a 2M solution of sodium borohydride in THF is added. The solution is stirred for 10 min. After this time, 24 mL of a 2M HCl solution in water is added. The resulting solution is diluted with ether, washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The resulting crude material is purified by column chromatography eluting with 40% EtOAc/hexanes to give the title compound (7.6 g, 22.5 mmol) as a white solid.

Fuente