Acetic Anhydride → HCID 66547000, compound

Participants

Reaction Steps

In an 100 ml round-bottom flask, 0.8 gram (2.0 mmoles) of 2-acetyl-4-hydroxy-9-[(tert-butoxycarbonyl)amino]acetoxy-naphtho[2,3-b]furan (prepared in example 12) was dissolved in 30 ml of DMF with mild heating. To the solution, added 0.9 ml of TEA and 0.5 ml of acetic anhydride. The mixture was sealed or isolated from air, and then had been stirred vigorously at room temperature overnight. After addition of 100 ml of ethyl acetate, the reaction mixture was extracted with 80 ml of ice-cooled aqueous 3% citric acid solution twice, and dried with anhydrous sodium sulfate. The organic phase was evaporated to dryness. Product was purified by silica gel chromatograph using dichloromethane as elution solvent. 0.6 gram (1.36 mmole) of product was obtained with yield of 68.0% and characterized by 1H NMR and mass spectrum. 1H NMR (in DMSO) δ 1.44 (s, 9H), 2.62 (s, 3H), 2.63 (s, 3H), 4.34 (d, J=6, 2H), 7.67-7.71 (m, 3H), 8.15-8.17 (m, 2H), 8.25 (s, 1H). Mass (M+H) is 442, Mass [M-(tert-butyl)+2H] is 386.

Provenance & Evidence