Potassium Carbonate → HCID 69889373, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,5-dimethyl-3-bromomethylfuran (5.95 mmol theor.) in DMF (30 mL) was added K2CO3 (1.64 g, 11.9 mmol) and tert-butylcarbazate (3.1 g, 23.8 mmol). The reaction was heated to 65° C. for 1 h. The reaction was cooled to room temperature, diluted with ethyl acetate and the layers separated. The organic layer was washed with saturated aqueous NH4Cl, water and brine and dried over Na2SO4. The mixture was filtered, concentrated and distilled on a Kuglerohr apparatus at 100° C. and 35 mTorr to remove the excess DMF and tert-butylcarbazate. This material was then purified using silica gel column chromatography (hexanes—4:1 hexanes:ethyl acetate as eluant) to afford the title compound as a dark yellow oil (670 mg, 2.79 mmol, 47% for the two steps). 1H NMR (300 MHz, DMSO-d6): δ 8.11 (br s, 1H); 5.91 (s, 1H); 4.38 (br s, 1H); 3.54 (s, 2H); 2.16 (s, 3H); 2.14 (s, 3H); 1.39 (s, 9H).

Provenance & Evidence