Water → HCID 22452670, compound

Participants

Reaction Steps

To a solution of methyl 3-hydroxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (Example 6 subpart (c)) (1.38 g, 6.69 mmol) in DMF (30 mL) was added NaH (0.32 g, 8.0 mmol). After stirring at room temperature for 1 h, dimethylsulfate (0.76 mL, 8.0 mmol) was added, the mixture stirred at room temperature for 1 h and water and Et2O was added. The separated organic layer was washed with brine, water, dried (MgSO4), filtered and concentrated. Following flash chromatography methyl 3-methoxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate was obtained as a colorless oil (900 mg, 61%). 1H NMR (CDCl3) δ 7.21 (d, 1H), 6.78 (d, 1H), 3.87 (s, 3H), 3.80 (s, 3H), 2.97 (s, 2H), 2.79 (s, 2H), 1.76 (m, 4H); MS m/z 221.1 (M+H).

Provenance & Evidence