Potassium Carbonate → Spiro(2.5)octane-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of spiro[2.5]octan-6-ylmethanol (1.83 g, 13 mmo) in dichloromethane (60 mL) was added NaHCO3 (30 mL of a 0.5 M aqueous solution) and K2CO3 (30 mL of a 0.05M aqueous solution) and tehn cooled to 0°C. TEMPO (0.203 g, 1.3 mmol), TBAC1 (0.361 g, 1.3 mmol), and NCS (0.36 g, 1.3 mmol) were added successively, and the reaction mixture was stirred at rt fo(4 h. Using a separation funnel the organic layer was collected and then washed with brine, dried over Na2SO4. The organics were concentrated in vacuo and the crude residue was purified by column chromatography on silica gel with a gradient of 20 to 60% hexane-DCM as eluant to afford the desired product spiro[2.5]octane-6-carbaldehyde. 1H NMR (400 MHz, CDCl3) δ 9.66 (d, J=0.8 Hz, 1H), 2.30 (m, 1H), 1.91-1.88 (m, 2H), 1.67-1.48 (m, 4H), 1.09-104 (m, 2H), 0.31-0.29 (m, 2H), 0.22-0.20 (m, 2H). MS m/z 139.0 (M+1).

Provenance & Evidence