反応 #43904

反応方程式

hydrochloric acid

Triisopropyl borate

4-(4-bromo-3,5-dimethylphenoxy)tetrahydro-2H-thiopyran

n-butyllithium hexane

→

title compound

収率 71.0%

[2,6-dimethyl-4-(tetrahydro-2H-thiopyran-4-yloxy)phenyl]boronic acid

収率 71.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred overnight, during which the mixture
2. 2
   温度cooled
3. 3
   workup.STIRRINGthe mixture was stirred for 2.5 hr
4. 4
   その他The aqueous layer and the organic layer were separated
5. 5
   洗浄the organic layer was washed with saturated brine and saturated aqueous sodium hydrogencarbonate
6. 6
   乾燥The organic layer was dried over anhydrous magnesium sulfate
7. 7
   濃縮concentrated under reduced pressure
8. 8
   洗浄The residue was washed with cool hexane

実験手順

To a solution of 4-(4-bromo-3,5-dimethylphenoxy)tetrahydro-2H-thiopyran (3.01 g, 10.0 mmol) in tetrahydrofuran (50 mL) was added dropwise n-butyllithium hexane solution (1.6 M, 6.57 mL, 10.5 mmol) at −78° C., and the reaction mixture was stirred for 1.5 hr at the same temperature. Triisopropyl borate (6.92 mL, 30.0 mmol) was added, and the mixture was stirred overnight, during which the mixture was allowed to warm to room temperature. The reaction mixture was ice-cooled, 2 M hydrochloric acid (50 mL) was added, and the mixture was stirred for 2.5 hr. The aqueous layer and the organic layer were separated, and the organic layer was washed with saturated brine and saturated aqueous sodium hydrogencarbonate while simultaneously adjusting to neutral. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with cool hexane to give the title compound (1.89 g, yield 71%) as colorless crystals.

出典