Acetic Anhydride → 2-Chloro-1,3-benzoxazol-6-yl acetate

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>ClCCl>[C:19]([O:18][C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([Cl:8])[O:10][C:11]=2[CH:17]=1)(=[O:21])[CH3:20]

Participants

Procedure

Triethylamine (1.48 ml) was added to a suspension of 2-chloro-1,3-benzoxazol-6-ol (1.63 g) [see Preparation 34] in dichloromethane (20 ml), and after 5 minutes acetic anhydride (1.01 ml) was added. The reaction mixture was stirred at room temperature for 18 hours, after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0, changing to 40:10, changing to 0:100, by volume, hexane:ethyl acetate to afford 2-chloro-1,3-benzoxazol-6-yl acetate (1.63 g) as an oil.