Реакция #512302

Уравнение реакции

tetradecylmagnesium chloride

triethyl borate

→

n-tetradecylboronic acid

Выход 93.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   Температураwarmed up slowly over 3 hours to room temperature
2. 2
   ДругоеMost of the solvent was removed on rotary evaporator
3. 3
   workup.ADDITIONthe concentrated mixture was poured into water (300 ml)
4. 4
   workup.STIRRINGAfter being stirred for 10 hours
5. 5
   Другоеprecipitated tetradecylboronic acid
6. 6
   Другоеwas isolated by filtration
7. 7
   Промывкаwashed three times with water
8. 8
   Другоеdried with air overnight
9. 9
   ПромывкаThe dried white solid was washed with cold hexane
10. 10
    Другоеto remove a trace of tetradecane
11. 11
    Другоеdried with air

Методика

To a stirred solution of tetradecylmagnesium chloride (50 ml, 1M in THF) was added at −20° C. to THF (50 ml) followed by triethyl borate (10.2 ml, 60 mmol). The reaction mixture was stirred briefly at −20° C., and warmed up slowly over 3 hours to room temperature. Most of the solvent was removed on rotary evaporator and the concentrated mixture was poured into water (300 ml) and pH of the mixture was adjusted to about pH 4 using 12N hydrochloric acid. After being stirred for 10 hours, precipitated tetradecylboronic acid was isolated by filtration, washed three times with water and dried with air overnight. The dried white solid was washed with cold hexane to remove a trace of tetradecane and dried with air to yield 11.3 g (93%) of n-tetradecylboronic acid.

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