反应详情

To a cold, stirring suspension of 1.3 gm hydroxylamine hydrochloride and 1.8 gm sodium carbonate in 25 ml CH2Cl2 was added dropwise 4 gms 9(3-methylphenyl)nonanoyl chloride. The reaction mixture was stirred at 5°-10° for 45 min, then 2.1 ml H2O was added and the mixture stirred overnight at room temperature. The suspension was then diluted with CH2Cl2 and water, shaken, and the organic layer was separated. It was washed three times with water and once with NaCl solution, dried over MgSO4, and filtered. The solvent was removed in vacuo to give an oil which solidified but which could not be crystallized. The solid was disolved in ether, shaken with 5% KOH, and the ether discarded. The aqueous layer was acidified and the precipitated solid extracted into CHCl3. The chloroform was washed twice with water and once with NaCl solution, dried over MgSO4, filtered, and evaporated in vacuo. The resulting oil was purified by silica gel column chromatography, using gradually increasing cocentrations of ethyl acetate in chloroform (0, 10%, 15%, 25%). Fractions containing the major component (detected by thin layer chromatography--Rf=0.4 in 1:1 ETOAc:CHCl3) were collected and evaporated down to give an off-white solid which was crystallized from CH2Cl2 :hexanes. Yield 1.3 gms (33%) product of m.p. 49°-50°. Elemental analysis: calculated C 72.98, H 9.57, N 5.32% found C 72.80, H 9.56, N 5.32%.

1. stirringThe reaction mixture was stirred at 5°-10° for 45 min
2. stirringthe mixture stirred overnight at room temperature
3. stirringshaken
4. customthe organic layer was separated
5. washIt was washed three times with water
6. dry with materialonce with NaCl solution, dried over MgSO4
7. filtrationfiltered
8. customThe solvent was removed in vacuo
9. customto give an oil which
10. customwhich could not be crystallized
11. stirringshaken with 5% KOH
12. extractionthe precipitated solid extracted into CHCl3
13. washThe chloroform was washed twice with water and once with NaCl solution
14. dry with materialdried over MgSO4
15. filtrationfiltered
16. customevaporated in vacuo
17. customThe resulting oil was purified by silica gel column chromatography
18. additionFractions containing the major component (detected by thin layer chromatography--Rf=0.4 in 1:1 ETOAc:CHCl3)
19. customwere collected
20. customevaporated down
21. customto give an off-white solid which
22. customwas crystallized from CH2Cl2