Реакция #77644

Уравнение реакции

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

Растворители

THF

water

water

THF

Условия реакции

Обработка

1. 1
   Температураat reflux for 2 hours
2. 2
   Температураthe medium is cooled
3. 3
   ФильтрацияAfter filtration
4. 4
   Другоеthe residue is purified by chromatography on silica gel (eluent: 95 heptane/5 ethyl acetate)

Методика

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).

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