Dimethylformamide → Methyl 5,6,7,8-tetrahydro-5-methoxy-2-naphthalenecarboxylate

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (80% oil dispersion, 28 mg, 0.93 mmol) was added to a solution of 2 (0.19 g, 0.93 mmol) in DMF (2 mL) stirring at 0° C. Methyl iodide (0.13 g, 58 mL, 0.93 mmol) was added. After stirring at 0° C. for 2 hours and at ambient temperature for 30 minutes, additional sodium hydride (14 mg, 0.47 mmol) and methyl iodide (29 mL, 0.47 mmol) were added. After stirring an additional 3 hours, the reaction was quenched with 0.1N HCl and transferred to a separatory funnel with CH2Cl2. Extraction with CH2Cl2 (2×40 mL) and drying over MgSO4 afforded 0.33 g of crude product after evaporation of the solvent. Flash chromatography (silica, 25 mm dia, 10% EtOAc/hexane) afforded 0.13 g (63%) of the title compound.

Provenance & Evidence