Reaction #157771

Reaction equation

water

tetrabutylammonium fluoride

6-[(E)-1-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-chlorophenyl)-2-cyclopentylethenyl]-3-ethyl-2-methoxypyridine

hydrochloric acid

→

2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenol

Yield 99.0%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Extractionfollowed by extraction with ethyl acetate
2. 2
   WashThe organic layer was washed with brine
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   OtherThe solvent was then evaporated under reduced pressure
6. 6
   OtherThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→1:1)

Procedure

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.73 mL) was added to a solution of 6-[(E)-1-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-chlorophenyl)-2-cyclopentylethenyl]-3-ethyl-2-methoxypyridine (409 mg) in tetrahydrofuran (3 mL) under ice-boiling, and the mixture was stirred at room temperature for two hours. The reaction solution was poured into water and made acidic with 1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→1:1) to give 2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenol as a yellow oil (306 mg, 99%).

Source