Imidazole → HCID 68650408, compound

Participants

Reaction Steps

5-(Hydroxyprop-1-yn-1-yl)-2,3-dihydro-1H-indene-1-one (1.03 g, 5.42 mmol) was dissolved in DMF and treated with chloro-tert-butyldimethylsilane (981 mg, 6.51 mmol), imidazole (443 mg, 6.51 mmol) at 0° C. The reaction mixture was allowed to reach ambient temperature. After 10 h, the reaction mixture was extracted with ethyl acetate (100 mL×3), washed with water, brine and dried over MgSO4. The organic layer was concentrated under vacuum and purified by flash column chromatography to yield the 5-(3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-2,3-dihydro-1H-inden-1-one (1.54 g, 94% yield): 1H NMR (400 MHz, CDCl3): δ 7.63 (d, 1H), 7.59 (s, 1H), 7.42 (d, 1H), 4.45 (t, 2H), 3.10 (m, 2H), 2.78 (m, 2H), 2.64 (m, 2H), 1.82 (m, 2H), 0.95 (s, 9H), 0.06 (s, 6H).

Provenance & Evidence