反应详情

To a warm stirred suspension of 3,4-dihydro-7-hydroxy-4-iminocoumarin (17.7g; 0.1 mole) in dry DMF (75 ml) was added sodium hydride (2.4; 0.1 mole) portionwise and the mixture refluxed for 1.5 hours to complete formation of the sodium salt. A solution of 1-chloro-3-phenoxy-2-propanol (18.7 g; 0.1 mole) in dry DMF (10 ml) was added dropwise at reflux and the mixture stirred at reflux for an additional 4 hours. The solvent was removed in vacuo and water (200 ml) added to the residue. The yellow solid was filtered off, washed well with water and dried in vacuo over P2O5 to give 30.0 g (92%) of crude product which was suitable for most purposes. Recrystallisation from ethyl acetate gave material of m.p. 213°-214°; νmax (mull) 3320, 3200, complex carbonyl region 1690-1590cm-1,. τ(DSMO); 5.82(5H, m); 5.35(2H, broad exchangeable s); 4.85(1H,s); 3.20-2.52(8H, m with 1 proton removed after D2O exchange); 2.02(1H, d.) (Found; C, 64.52; H, 5.26; N, 3.78; C18H17NO5 0.5H2O requires; C, 64.28; H, 5.39; N, 4.16%).

1. temperaturethe mixture refluxed for 1.5 hours
2. temperatureat reflux
3. stirringthe mixture stirred
4. temperatureat reflux for an additional 4 hours
5. customThe solvent was removed in vacuo and water (200 ml)
6. additionadded to the residue
7. filtrationThe yellow solid was filtered off
8. washwashed well with water
9. dry with materialdried in vacuo over P2O5