HCID 474081, compound → HCID 474087, compound

Reaction equation

C([O:4][CH2:5][CH2:6][N:7]1[C:11]([S:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)=[C:10]([CH:21]([CH3:23])[CH3:22])[N:9]=[C:8]1[CH2:24][CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.O>[CH2:27]([O:26][CH2:25][CH2:24][C:8]1[N:7]([CH2:6][CH2:5][OH:4])[C:11]([S:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)=[C:10]([CH:21]([CH3:23])[CH3:22])[N:9]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Procedure

In 30 ml of dry diethyl ether was dissolved 3.0 g (5.9 mmol) of the ester compound (130c), followed by addition of 230 mg (6 mmol) of lithium aluminum hydride under ice-cooling, and the mixture was stirred at room temperature for 15 minutes. The mixture was diluted with water, extracted with ethyl acetate, the extract was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and further recrystallized from ethyl acetate-n-hexane to give 2.5 g of 2-(2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-1-yl)ethanol (130d) as crystals (yield 91%). mp 129-130° C.