[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:6]3-hydroxy benzaldehyde/ethyl 2-bromoacetate (1.1 eq) and K2CO3 (2 eq) were taken in DMF and heated at 80° C. for 16 h when TLC indicated completion of reaction. The reaction mixture was cooled to rt and poured into water. Extraction was done with DCM. The combined organic extracts was dried, concentrated and purified by column chromatography using silica gel (100-200 mesh) to afford the pure product (23%) as a colorless oil. NMR: δ 1.298 (t, J=7.2 Hz, 3H), 4.27 (q, J=7.2 Hz, 2H), 4.683 (s, 1H), 7.20-7.27 (m, 1H), 7.361 (s, 1H), 7.42-7.52 (m, 2H), 9.96 (s, 1H).
Loading…
