Water → 5-(Methoxymethoxy)-6-nitroindane

Participants

Reaction Conditions

Reaction Steps

1.04 g of 55% sodium hydride/paraffin oil was suspended in 40.0 mL of DMF, and a solution of 3.90 g of 6-nitroindan-5-ol in DMF (10.0 mL) was added dropwise thereto at 5° C. over 15 minutes, followed by stirring at 5° C. for 30 minutes. To the reaction liquid was added dropwise 2.15 mL of methoxymethyl chloride over 5 minutes, followed by stirring at room temperature for 1 hour. To the reaction liquid was added water, followed by extraction with ethyl acetate, and the organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20) to obtain 4.20 g of 5-(methoxymethoxy)-6-nitroindane.

Provenance & Evidence