Methyl iodide → HCID 13082495, compound

Participants

Reaction Steps

To a suspension of 60% NaH in an oil dispersion (20 g, 500 mmol) in THF (600 mL) at 0° C. is added a solution of α-tetralone (24.8 g, 166.5 mmol) in THF (40 mL) via cannula, followed by iodomethane (119 g, 833 mmol). The reaction is permitted to warm to room temperature and after one hour is quenched with 1 M aqueous sodium bisulfate. The reaction mixture is partitioned between water and ethyl acetate and the organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The resulting residue is then dissolved in methanol (600 mL) and dichloromethane (100 mL). Sodium borohydride (37.8 g, 262 mmol) is then added in five portions over 20 minutes. After one hour the reaction is diluted with water, and the organic solvents are then evaporated in vacuo. The resulting mixture is extracted with ethyl acetate, and the organic extract is dried with magnesium sulfate, filtered and concentrated. The resulting residue is then dissolved in dichloromethane (300 mL). To the resulting solution is added triethylamine (50 g, 490 mmol) and 4-dimethylaminopyridine (4 g, 33 mmol). The reaction is cooled to 0° C. and charged with acetic anhydride (42 g, 408 mmol). The reaction is permitted to stir for 10 minutes, then is diluted with ethyl acetate, and washed with 1 M aqueous NaHSO41 followed by saturated aqueous NaHCO3. The organic phase is dried with magnesium sulfate, filtered, and concentrated. The resulting oil is then purified by distillation (110° C. at 0.2 torr) to furnish acetic acid 2,2-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl ester; 1H NMR (400 MHz, CDCl3) δ ppm 0.95 (s, 3 H), 1.01 (s, 3 H), 1.50-1.63 (m, 1 H), 1.84-1.99 (m, 1 H), 2.10 (s, 3 H), 2.76-2.94 (m, 2 H), 5.74 (s, 1 H), 7.08-7.31 (m, 4 H).

Provenance & Evidence