Diethyl Ether → 3-(Triisopropyl-siloxyethyl)-cyclobutanone

Participants

Reaction Conditions

Reaction Steps

Zinc dust (25.5 g, 0.39 mol) was added to a solution of 3-(triisopropyl-siloxyethyl)-2,2-dichlorocyclobutanone (22.21 g, 65.4 mmol) in glacial acetic acid (110 mL) at room temperature. The reactants were heated at 60° C. for 1 hr, after which time dry diethyl ether was added to the cooled products, which were then filtered. The residue was washed with diethyl ether and the combined filtrate and washings were concentrated under reduced pressure. The residue was dissolved in dichloromethane, which was washed with saturated NaHCO3 twice and water once. The organic phase was dried over MgSO4 and the solvent was evaporated to give an oily product, which was purified by silica gel flash chromatography (Hexane: EtOAc=12:1) to give a colorless oil. 1H NMR (CDCl3, 400 MHz): δ 1.03-1.08 (m, 21H), 1.80-1.85 (m, 2H), 2.49-2.60 (m, 1H), 2.71-2.80 (m, 2H), 3.12-3.21 (m, 2H), 3.74-3.77 (t, J=6.0, 2H). 13C NMR (CDCl3, 100 MHz): δ 12.12, 18.22, 21.38, 39.36, 52.92, 62.37, 209.00. MS (FAB): expected for C15H30O2Si (M+H)+ 271.48. Found 271.20887. IR (neat) νmax 3053, 2925, 2866, 1778, 1462, 1265, 1103, 1013, 883, 740, 705.

Provenance & Evidence