Sodium Hydroxide → HCID 86629954, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methylcarbazole (500 mg, 2.76 mmol) in toluene (7.5 mL), was added sodium hydroxide (5 g, 125 mmol) as a solution in water (15 mL) followed by tri n-butyl benzyl ammonium chloride (25 mg). The two-phase solution was stirred at about 0° C. and di t-butylcarbonate (1.25 g, 5.7 mmol) was added in one portion. The mixture was stirred for about 1 h at about 0° C., the toluene layer was separated and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with water (2×10 mL); dried (MgSO4) and concentrated under in vacuo to afford the crude product (725 mg, 96% yield). ES-MS (M+H)+ 282.0 (calc. 282.1).

Provenance & Evidence