Imidazole → HCID 18618529, compound

Participants

Reaction Steps

A solution of 3.47 g of (2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran 7 in 30 mL of CH2Cl2 was taken in an 100 mL round bottom flask equipped with a magnetic stir bar and nitrogen inlet. That solution was cooled in an ice-water bath and 2.18 g (0.032 mol) of imidazole was added, followed by a solution of 3.6 g (0.024 mol) of tert-butyldimethylsilylchloride (TBDMSCl) in 30 mL of CH2Cl2. The reaction mixture then was stirred at room temperature for 3 hours, and the reaction then quenched with ice water, the organic layer separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography using light petroleum ether:ethyl acetate (9:1) to yield (2S) (4-fluorophenoxymethyl)-5-(tert-butyldimethylsiloxy)-tetrahydrofuran) 8 as an oil (5.1 g, 95%). 1H NMR (200 MHz, CDCl3): δ0.09 (s, 6H), 0.88 (s, 9H), 1.72-2.34 (m, 4H), 3.76=4.08 (m, 2H), 4.28-4.54 (m, 1H), 5.47. (s, 1/3H), 5.54 (d, J=4.5 Hz, 2/3H), 6.75-7.0 (m, 4H).

Provenance & Evidence