Hydrochloric Acid → HCID 66584683, compound

Participants

Reaction Steps

To a solution of 5.5 mL (12.28 mmoles) of 2.2 M n-butyl lithium diluted with 20 mL of anhydrous tetrahydrofuran in an ice bath, 1.4 gram (6.14 mmoles) of 4,9-dimethoxy-naphtho[2,3-b]furan in 20 mL of anhydrous tetrahydrofuran was added dropwise over 5 minutes. The mixture was further stirred for 40 minutes in ice bath, and then 0.95 mL (12.28 mmoles) of N,N-dimethylformamide was added dropwise over 5 minutes. The mixture was stirred for additional 30 minutes in ice bath, and then further stirred for 120 minutes at room temperature. The reaction mixture was stopped by addition of 100 mL 0.1N hydrochloric acid, and then evaporated to remove tetrahydrofuran. The remaining aqueous solution was extracted with dichloromethane twice. The combined organic phase was washed with water, dried with anhydrous sodium sulfate, and evaporated to dryness. Product was purified by silica gel chromatograph using dichloromethane as elution solvent. 1.20 gram (4.69 mmoles) of product was obtained with yield of 76% and characterized by 1H NMR and mass spectrum. 1H NMR (in CDCl3) δ 4.30 (s, 3H), 4.34 (s, 3H), 7.47-7.51 (m, 1H), 7.55-7.59 (m, 1H), 7.89 (s, 1H), 8.29-8.33 (m, 2H), 9.95 (s, 1H). Mass (M+H) is 257.

Provenance & Evidence