Реакция #1914825

Уравнение реакции

BH3.THF

16-bromohexadecanoic acid

→

desired product

Выход 93.2%

16-Bromohexadecan-1-ol

Выход 93.2%

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеReaction mixture
2. 2
   Другоеadditional 1 hr
3. 3
   Другоеat RT
4. 4
   workup.ADDITIONAfter that time the resulted mixture was poured
5. 5
   workup.STIRRINGwith stirring, into a vessel
6. 6
   ЭкстракцияOrganic compounds were extracted with 3×200 ml of ether
7. 7
   Сушкаdried over sodium sulfate
8. 8
   ДругоеAfter removal of ether material
9. 9
   workup.DISSOLUTIONwas dissolved in minimum amount of dicloromethane
10. 10
    Другоеpurified by silica gel chromatography (100% dicloromethane as eluent)

Методика

Under inert atmosphere 10 ml of BH3.THF complex (1.0 M THF solution) were added to 30 ml THF solution of 2.15 gr (6.41 mmole) of 16-bromohexadecanoic acid at −20° C. Reaction mixture was stirred at this temperature for 2 hrs and then additional 1 hr at RT. After that time the resulted mixture was poured, with stirring, into a vessel containing 200 ml of ice/saturated sodium bicarbonate aqueous solution. Organic compounds were extracted with 3×200 ml of ether. The ether fractions were combined and dried over sodium sulfate. After removal of ether material was dissolved in minimum amount of dicloromethane and purified by silica gel chromatography (100% dicloromethane as eluent). 1.92 gr (93% yield) of the desired product were obtained.

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