Reacción #1839022

Ecuación de reacción

product

4-[2-(tert-butyldimethylsilanyloxy)ethoxymethyl]benzoic acid methyl ester

lithium aluminum deuteride

→

oil

Rendimiento 87.5%

{4-[2-(tert-butyldimethylsilanyloxy)ethoxymethyl]phenyl}methanol

Rendimiento 87.5%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas removed
2. 2
   workup.ADDITIONThe reaction was then diluted with water
3. 3
   Extracciónextracted with ethyl acetate (2 times)
4. 4
   SecadoThe combined organics were dried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a solution of the product of Example 8B (610 mg, 1.857 mmol) in THE (19 mL) at 0° C. was added a 1M solution (in THF) of lithium aluminum deuteride (1.9 mL, 1.857 mmol) dropwise. After completion of addition the ice bath was removed and the reaction was stirred at room temperature for 3.5 hours under nitrogen atmosphere, monitoring by TLC (3:1 pentane:ethyl acetate). The reaction was then diluted with water and extracted with ethyl acetate (2 times). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to obtain a clear oil (482 mg, 86% yield). The material was taken to the next step without further purification. 1H NMR (600 MHz, CDCl3): 7.33 (s, 4H), 4.56 (s, 2H), 0.89 (s, 9H), 0.06 (s, 6H).

Fuente