Homovanillic Acid → HCID 22600136、化合物

反応式

C([O-])([O-])=O.[Cs+].[Cs+].[C:7]([OH:19])(=[O:18])[CH2:8][C:9]1[CH:17]=[CH:16][C:14]([OH:15])=[C:11]([O:12][CH3:13])[CH:10]=1.[CH:20]1[CH:25]=[CH:24][C:23]([CH2:26]Br)=[CH:22][CH:21]=1>CC#N>[CH2:26]([O:15][C:14]1[CH:16]=[CH:17][C:9]([CH2:8][C:7]([O:19][CH2:8][C:9]2[CH:17]=[CH:16][CH:14]=[CH:11][CH:10]=2)=[O:18])=[CH:10][C:11]=1[O:12][CH3:13])[C:23]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

参加物

実験手順

Cs2CO3 (17.88 g; 54.9 mmol) was added to a solution of homovanillic acid (2.0 g; 11 mmol) in CH3CN, whereafter BnBr (4.3 g; 24.15 mmol) was added dropwise over 10 minutes. The mixture was refluxed overnight, filtered through Hyflo and concentrated. The resulting mixture was dissolved in EtOAc (100 mL), water (30 mL) was added, and the aqueous layer was separated. The organic phase was washed with citric acid solution (5%, 1×20 mL) and brine, dried (Na2SO4), and evaporated to yield 4.25 g (quant.) of the sub-title compound.