تفاعل #217464

معادلة التفاعل

BH3.THF

16-bromohexadecanoic acid

→

desired product

المردود 93.2%

16-Bromohexadecan-1-ol

المردود 93.2%

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر