Reacción #77644

Ecuación de reacción

lithium aluminium hydride

sodium methoxide

sodium hydroxide

(E)-6-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}-1,1,1,-trifluoro-2-trifluoromethyloct-5-en-3-yn-2-ol

→

desired product

(3E,5E)-6-{5-[3,4-bis(tert-Butyldimethylsilanyl-oxymethyl)phenoxymethyl]-2-thienyl}-1,1,1-trifluoro-2-trifluoromethylocta-3,5-dien-2-ol

Disolventes

THF

water

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 2 hours
2. 2
   Temperaturathe medium is cooled
3. 3
   FiltraciónAfter filtration
4. 4
   Otrothe residue is purified by chromatography on silica gel (eluent: 95 heptane/5 ethyl acetate)

Procedimiento

1 g (1.3 mmol) of (E)-6-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}-1,1,1,-trifluoro-2-trifluoromethyloct-5-en-3-yn-2-ol is dissolved in 10 mL of THF and then added to a suspension of 160 mg (4.2 mmol) of lithium aluminium hydride and 450 mg (8.4 mmol) of sodium methoxide in 20 mL of THF. After stirring at reflux for 2 hours, the medium is cooled and then treated with 200 μL of water, 200 μL of 15% sodium hydroxide and 600 μL of water. After filtration, the residue is purified by chromatography on silica gel (eluent: 95 heptane/5 ethyl acetate). The desired product is obtained in the form of a yellow oil (210 mg).

Fuente