반응 #1620054

반응 방정식

(S)-3-cyclohexyl-1,2-propanediol

triethylamine

2,4,6-triisopropylbenzenesulfonyl chloride

→

oil

수율 75.0%

(S)-Cyclohexylmethyloxirane

수율 75.0%

용매

CH2Cl2

ether

반응 조건

후처리

1. 1
   여과filtered through celite
2. 2
   농축concentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethanol (100 mL)
4. 4
   workup.ADDITION1M NaOH was added (32 mL)
5. 5
   workup.WAITAfter 30 min
6. 6
   농축the reaction was carefully concentrated
7. 7
   workup.ADDITIONdiluted with water (100 mL)
8. 8
   추출extracted into ether (3×50 mL)
9. 9
   세척The organic extracts were washed with brine (20 mL)
10. 10
    건조dried (MgSO4)
11. 11
    여과filtered
12. 12
    농축concentrated
13. 13
    기타to give a colorless aromatic oil which
14. 14
    기타was purified first by passage through a plug of silica gel eluting with 5%EtOAc/hexane
15. 15
    workup.DISTILLATIONby bulb-to-bulb distillation under reduced pressure

실험 절차

To a solution of (S)-3-cyclohexyl-1,2-propanediol in CH2Cl2 was added triethylamine (6.6 mL), 2,4,6-triisopropylbenzenesulfonyl chloride (11.5 g), and DMAP (0.386 g). After 14 h, the reaction was diluted with ether, chilled to 0° C., filtered through celite and concentrated. The residue was dissolved in ethanol (100 mL), and 1M NaOH was added (32 mL). After 30 min, the reaction was carefully concentrated, diluted with water (100 mL) and extracted into ether (3×50 mL). The organic extracts were washed with brine (20 mL), dried (MgSO4), filtered and concentrated to give a colorless aromatic oil which was purified first by passage through a plug of silica gel eluting with 5%EtOAc/hexane, then by bulb-to-bulb distillation under reduced pressure to give a colorless aromatic oil (3.3 g, 75%). 1H NMR (300 MHz, CDCl3) δ0.90-1.09 (m, 2H), 1.10-1.85 (m, 11H), 2.43 (dd, J=5.1, 2.7 Hz, 1H), 2.75 (dd, J=5.1, 4.5 Hz, 1H), 2.94 (m, 1H).

출처