Imidazole → HCID 59671393, compound

Participants

Reaction Steps

In an oven-dried 2 L two-neck flask, cooled under nitrogen, to a solution of (1S,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopent-2-en-1-ol (11) (98.07 g, 0.3864 mol) in methylene chloride (500 mL, 8 mol) was added 1H-imidazole (31.57 g, 0.4637 mol). To the resulting yellow solution was added a solution of tert-butyldimethylsilyl chloride (58.2 g, 0.386 mol) in methylene chloride (300 mL, 5 mol) via addition funnel over ˜30 min. The mixture was stirred mechanically for 18 hours. The reaction was quenched via addition of water (500 mL) and the layers were separated. The organic layer was washed with water (2×500 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford tert-butyl[((1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopent-3-en-1-yl)methoxy]dimethylsilane (143.3 g) as a crude residue that was used without further purification.

Provenance & Evidence