Acetyl chloride → 1-[3-(Methoxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethan-1-one
Reaction equation
[CH3:1][C:2](N(C)C)=[O:3].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][O:12][CH2:13][CH:14]1[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][CH2:15]1.C(Cl)(=O)C>>[CH3:11][O:12][CH2:13][CH:14]1[CH2:15][O:16][C:17]2[CH:23]=[CH:22][C:21]([C:2]([CH3:1])=[O:3])=[CH:20][C:18]=2[O:19]1Participants
5
Procedure
Dimethyl acetamide (16.65 mol, 1.31 ml) was added slowly to anhydrous aluminum chloride (33.3 mmol, 4.44 g) at 0° C. in the presence of nitrogen and stirred for 30 min at a room temperature, and then, the titled compound prepared in Example 1 (3.77 mmol, 500 mg) was added slowly to the resulting mixture, followed by stirring for 15 min. Then, acetyl chloride (3.33 mmol, 0.28 ml) was added and stirred for 5 hours at a room temperature. Ice was added slowly to the mixture to destroy and remove the remaining aluminum chloride. The reaction mixture was neutralized with NaHCO3, extracted with ethylacetate, followed by removing the solvent. And then, the resultant was dried to prepare the titled compound (520 mg, 84%).