Sodium hydride → HCID 68642095, compound

Reaction equation

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

Participants

Procedure

To N,N-dimethylformamide (2 ml), 2-[2-(2,4-dimethylphenyl)-4-methylthiazol-5-yl]-2,2-dimethoxyethanol (100 mg) prepared in the Step 31-1-2 and 4-methoxybenzyl chloride (61 mg) were added, and 60% sodium hydride suspension in oil (20 mg) was added thereto under an argon atmosphere. Then, the mixture was stirred at a room temperature for 4 hours. Ice water was added to the reaction solution, and then the mixture was subjected to extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then concentrated under a reduced pressure. The residue was purified by thin-layer chromatography (hexane:ethyl acetate=3:1) to give the title compound (90 mg, 64%).