Sodium Chloride → 4-(3',3'-Dimethylacryloxymethyl)-4-ethyl-2-oxazolidinone

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[CH2:1]([C:3]1([CH2:9][OH:10])[CH2:7][O:6][C:5](=[O:8])[NH:4]1)[CH3:2].[CH3:11][C:12]([CH3:17])=[CH:13][C:14](Cl)=[O:15].[Na+].[Cl-]>C(Cl)(Cl)Cl>[CH3:11][C:12]([CH3:17])=[CH:13][C:14]([O:10][CH2:9][C:3]1([CH2:1][CH3:2])[CH2:7][O:6][C:5](=[O:8])[NH:4]1)=[O:15]

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실험 절차

3.1 grams (0.021 mole) 4-ethyl-4-hydroxymethyl-2-oxazolidinone, prepared identically to that discussed in example 1, 2.6 grams (0.022 mole) 3,3-dimethylacryloyl chloride, and 25 milliliters chloroform were mixed in a one-necked round-bottom flask. The procedure employed was identical to that discussed in example 4. 4.10 grams (90% of the yield theoretically expected) of pure product was obtained as a yellow oil. The product exhibited the following spectral data: 1H NMR (CDCl3) δ0.98(t, 3H J=1.2 Hz), 1.65-1.71(m, 2H), 1.92(s, 3H), 2.17(s, 3H), 4.04-4.23(m. 4H), 5.71(s, 1H), 6.43(s, 1H); 13C NMR (CDCl3) δ7.6, 20.6, 27.7, 28.7, 60.3, 66.1, 71.3, 115.2, 159.0, 159.5, 166.2; IR (NaCl) 3215, 3020, 2970, 1785 cm−1; MS m/z 227. This monomer can be chlorinated or brominated by the same procedure as in example 1.