Imidazole → HCID 20517420, compound

Participants

Reaction Steps

Imidazole (2.45 g, 31.6 mmol) is added to a solution of (±) 5-hydroxy-2-methylcycloheptanone (2.03 g, 14.3 mmol) in dimethylformamide (35 ml) at 0° C. followed by t-butyldimethylsilyl chloride (2.38 g, 15.7 mmol) under nitrogen. The mixture is stirred at room temperature for 17 hours and then diluted with ether (100 ml) and washed three times with water. After drying (Na2SO4), the ether is removed in vacuo to afford (±) 5-t-butyldimethylsilyloxy-2-methylcycloheptanone (3.7 g, 100%). IR (neat)μ: 5.88 (C=O); NMR (CDCl3)δ: 0.1 (s, 6H, Si(CH3)0.93 [s, 9H, Si(CH3)2 --C(CH3)3 ], 1.1 (d, J=2--CH3), 3.6-4.2 (m, 1H, 5-H).

Provenance & Evidence