Imidazole → HCID 86693776, compound

Participants

Reaction Steps

To a solution of 2-methylcyclopent-2-en-1-ol (23.06 g, 235.0 mmol), 1H-imidazole (32.0 g, 470 mmol) and N,N-dimethyl-4-pyridinamine (5.74 g, 47.0 mmol) in dichloromethane (470 mL) at room temperature is added tert-butylchlorodiphenylsilane (90.41 g, 328.94 mmol) over 15 min. After stirring the reaction mixture at room temperature for 16 h, water (300 mL) is added and the layers are separated. The aqueous layer is extracted with dichloromethane (2×200 mL). The combined organic portions are dried over sodium sulfate, filtered, and concentrated to give the crude product (108 g) as a colorless oil. The crude product is purified in 20 g batches on 330 g silica gel using 0-20% dichloromethane/hexane (product observed on TLC using KMnO4 staining) to give the title compound as a colorless oil (25.3 g, 32%). 1H-NMR (400 MHz, CDCl3) δ 7.72-7.69 (m, 4H), 7.44-7.41 (m, 6H), 5.44-5.41 (m, 1H), 4.72-4.70 (m, 1H), 2.33-2.29 (m, 1H), 2.06-2.01 (m, 2H), 1.74-1.69 (m, 1H), 1.66-1.65 (m, 3H), 1.09 (s, 9H).

Provenance & Evidence