[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]=1[OH:11])[CH:6]=[O:7].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][CH2:28][CH3:29].C(Cl)Cl>CN(C=O)C.O>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]=1[O:11][CH2:27][CH2:28][CH3:29])[CH:6]=[O:7]64.5 g of 3-Methylthio-4-hydroxy-5benzyloxybenzaldehyde dissolved in a 75 mL of DMF was treated with 50 g of K2CO3 and 32 g of 1-bromopropane and stirred overnight at 70°. The next day about 1.5 liters of methylene chloride and an equal amount of water was added to the reaction mixture. The organic layer was removed, washed three times with distilled water, dried over MgSO4 and evaporated to a viscous liquid that solidified slowly: NMR(200 MHz, CDCl3) δ 1.02 (t, CH2CH2CH3), 1.82(m, CH2CH2CH3), 2.48(s, SCH3), 4.12(t, OCH2CH2CH3), 5.18(s, OCH2Ar), 7.26-7.52(m, ArH), 9.86(s, ArCHO).
Loading…
