Reaktion #730146

Reaktionsgleichung

sodium hydroxide

triisopropyl borate

tributyl-(2-methylpropoxy)methyl-tin

n-butyllithium

→

title compound

Ausbeute 29.0%

(2-Methylpropoxy)methyl boronic acid

Ausbeute 29.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 50 minutes
2. 2
   ExtraktionThe resultant was extracted three times
3. 3
   Waschenthe resulting aqueous layer was washed with diethyl ether
4. 4
   workup.ADDITIONThen, to the resulting aqueous layer was added 5N aqueous hydrochloric acid solution
5. 5
   Extraktionfollowed by extraction with diethyl ether three times
6. 6
   WaschenThe resulting organic layer was washed with an aqueous saturated sodium chloride solution
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   workup.DISTILLATIONThe solvent was distilled off from the filtrate

Vorschrift

To a solution of tributyl-(2-methylpropoxy)methyl-tin (1.00 g, 2.65 mmol) in tetrahydrofuran (20 ml) was added dropwise n-butyllithium (1.54M n-hexane solution, 1.72 ml, 2.65 mmol) at −78° C. (external temperature) under the nitrogen atmosphere, and the reaction mixture was stirred at the same temperature for 35 minutes. Then, to the reaction mixture was added triisopropyl borate (1.10 ml, 4.74 mmol) at −78° C. (external temperature) under the nitrogen atmosphere, and the reaction mixture was stirred at room temperature for 50 minutes. To the reaction mixture was added a 1N aqueous sodium hydroxide solution at room temperature. The resultant was extracted three times, and the resulting aqueous layer was washed with diethyl ether. Then, to the resulting aqueous layer was added 5N aqueous hydrochloric acid solution to make the solution acidic, followed by extraction with diethyl ether three times. The resulting organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was distilled off from the filtrate to obtain the title compound (101 mg, 0.765 mmol, 29%).

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