反应 #833543

反应方程式

16-bromohexadecanoic acid

→

desired product

收率 93.2%

16-Bromohexadecan-l-ol

收率 93.2%

溶剂

THF

THF

反应条件

后处理

1. 1
   其他Reaction mixture
2. 2
   其他additional 1 hr
3. 3
   其他at RT
4. 4
   workup.ADDITIONAfter that time the resulted mixture was poured
5. 5
   workup.STIRRINGwith stirring, into a vessel
6. 6
   萃取Organic compounds were extracted with 3×200 ml of ether
7. 7
   干燥dried over sodium sulfate
8. 8
   其他After removal of ether material
9. 9
   workup.DISSOLUTIONwas dissolved in minimum amount of dichloromethane
10. 10
    其他purified by silica gel chromatography (100% dichloromethane as eluent)

实验过程

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 dichloromethane and purified by silica gel chromatography (100% dichloromethane as eluent). 1.92 gr (93% yield) of the desired product were obtained.

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