반응 #833543

반응 방정식

16-bromohexadecanoic acid

→

desired product

수율 93.2%

16-Bromohexadecan-l-ol

수율 93.2%

용매

THF

THF

반응 조건

후처리

1. 1
   기타Reaction mixture
2. 2
   기타additional 1 hr
3. 3
   기타at RT
4. 4
   workup.ADDITIONAfter that time the resulted mixture was poured
5. 5
   workup.STIRRINGwith stirring, into a vessel
6. 6
   추출Organic compounds were extracted with 3×200 ml of ether
7. 7
   건조dried over sodium sulfate
8. 8
   기타After removal of ether material
9. 9
   workup.DISSOLUTIONwas dissolved in minimum amount of dichloromethane
10. 10
    기타purified by silica gel chromatography (100% dichloromethane as eluent)

실험 절차

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.

출처