반응 #952964

반응 방정식

THF

3-tert-butoxy-1,2-propane diol

→

liquid

1-tert-butyloxy-2,3-di-(2-methoxy ethoxy)propane

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도maintained
3. 3
   온도at reflux under an atmosphere of dry nitrogen for 24 hours
4. 4
   온도to cool
5. 5
   여과filtered
6. 6
   기타the solvent was removed by evaporation under vacuum
7. 7
   추출The residue was extracted with chloroform
8. 8
   건조dried (MgSO4)
9. 9
   여과filtered
10. 10
    기타solvent removed by vacuum rotary evaporation

실험 절차

Compound 21 (31.0 g, 0.135 mol.) was added to a slurry of the di-sodium salt of 3-tert-butoxy-1,2-propane diol, (0.062 mol.), 17, in refluxing in dry THF (500 ml). The reaction mixture was stirred, heated and maintained at reflux under an atmosphere of dry nitrogen for 24 hours. The mixture was allowed to cool and filtered and the solvent was removed by evaporation under vacuum. The residue was extracted with chloroform, dried (MgSO4) filtered and solvent removed by vacuum rotary evaporation to yield a brown liquid (17.0 g). The crude product was washed with water (250 ml) and extracted with chloroform (300 ml). The organic fraction was separated from the aqueous and dried (MgSO4) filtered. The solvent was removed by rotary evaporation under vacuum to give a pale yellow oil (15.0 g, 94%). The crude product was distilled (bpt. 120°-125° C., 0.25 torr) to give a colorless oily liquid (11.1 g, 67%): IR 2975, 2875 (CH) cm-1, 1198 (COC) cm-1, 1108 (COC) cm-1, 1H-NMR (CDCl3), d (ppm) 3.3-3.85 (m, 19H), 1.3 (s, 9H, tert-butyl), 13C-NMR (CDCl3), d, (ppm) 78.95, 72.94, 72.21, 71.92, 71.74, 70.64, 69.69, 61.73, 58.98, 58.8, 27.43. Mass spectroscopy, m/e: 264 M+ ; 208 (M-C(CH3)3)+ base peak.

출처