1,3-Dichloropropane → 3-(3-Chloropropyl)-2-oxazolidinone

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Reaction Steps

To a mechanically stirred, room temperature suspension of NaH (0.305 mole, hexane washed) in 50 mL of DMF under N2, was added 2-oxazolidinone (0.287 mole) portion wise. After stirring the resulting gelatinous mixture overnight, 1,3-dichloropropane (0.643 mole) was added and the mixture stirred 4 days at room temperature. The volatiles were then removed in vacuo and the resulting white residue taken up in CH2Cl2 and washed with H2O and brine, and dried over MgSO4. After filtration, the material was passed through a short column (SiO2 : EtOAc/Hex) to give (XVI) as a clear oil in 95% yield: 1H NMR (CDCl3) δ4.22 (t, 2H, J=6.6 Hz), 3.47 (m, 4H), 3.24 (t, 2H, J=7.0 Hz), and 1.98 (p, 2H, J=6.5 Hz); 13C NMR (CDCl3) δ158.5, 61.8, 45.0, 42.0, 41.8, and 30.2. Anal. Calcd for C6H10ClNO2 : C, 44.05; H, 6.16; N, 8.56. Found: 41.17; H, 5.77; N, 8.26.

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