反应详情

286 mg (1 mmol) of stearic acid (7) are mixed with 151 mg (1.2 mmol) of N-hydroxypyridine-2-thione, 183 mg (1.5 mmol) of p-dimethylaminopyridine (DMAP) and 310 mg (1.5 mmol) of dichlorohexylcarbodiimide (DCC). The mixture in 20 ml of benzene is stirred under an atmosphere of nitrogen and the solution obtained is brought to reflux so as to distil 10 ml of benzene. After 45 minutes under reflux, 10.8 ml (3 mmol) of tri-n-butylstannane and 10 mg of azobis(isobutyronitrile) (AIBN) in 10 ml of benzene are added dropwise during 15 minutes. Heating under reflux is continued for 6 hours, 10 ml of carbon tetra-chloride are then added, and refluxing is continued for one hour before evaporating the mixture to dryness. The residue is treated with iodine (20% in 10 ml CH2Cl2) and potassium fluoride (10% in 10 ml H2O), and the two phases are then vigorously stirred for 10 minutes. The polymeric tin residues are filtered under vacuum on Celite and washed with 5 ml of dichloromethane. The organic phase is removed and the aqueous layer is extracted twice with dichloromethane (2×10 ml). The combined organic phases are washed with sodium thiosulfate (10%, 10 ml) and 10 ml of water, dried over sodium sulfate, filtered and evaporated to dryness. The crude product purified by filtration on silica gel (100% pentane) gives 228 mg of n-heptadecane (8).

1. customthe solution obtained
2. temperatureto reflux so as
3. customto distil 10 ml of benzene
4. temperatureAfter 45 minutes under reflux
5. temperatureHeating
6. temperatureunder reflux
7. temperaturerefluxing
8. waitis continued for one hour
9. custombefore evaporating the mixture to dryness
10. additionThe residue is treated with iodine (20% in 10 ml CH2Cl2) and potassium fluoride (10% in 10 ml H2O)
11. filtrationThe polymeric tin residues are filtered under vacuum on Celite
12. washwashed with 5 ml of dichloromethane
13. customThe organic phase is removed
14. extractionthe aqueous layer is extracted twice with dichloromethane (2×10 ml)
15. washThe combined organic phases are washed with sodium thiosulfate (10%, 10 ml) and 10 ml of water
16. dry with materialdried over sodium sulfate
17. filtrationfiltered
18. customevaporated to dryness
19. filtrationThe crude product purified by filtration on silica gel (100% pentane)