反応 #833543

反応方程式

16-bromohexadecanoic acid

→

desired product

収率 93.2%

16-Bromohexadecan-l-ol

収率 93.2%

溶媒

THF

THF

反応条件

後処理

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

実験手順

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.

出典