Sodium hydride → 3,4-Dihydro-7-(2-hydroxy-3-phenoxypropoxy)-4-iminocoumarin

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Reaction Steps

To a warm stirred suspension of 3,4-dihydro-7-hydroxy-4-iminocoumarin (17.7 g; 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 mol) 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 1690-1590 cm-1,. τ(DSMO); 5.82(5H, m); 5.35(2H, broad exchangeable s); 4.85(1H, s); 3.2-2.52(8H, m with 1 proton removed after D2O exchange); 2.02(1H, d,) (Found: C, 64.52; H, 5.26; N, 3.78; C18H17NO5 0.5 H2O requires; C, 64.28; H, 5.39; N, 4.16%). By the same procedure the compounds in Table III were prepared.

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