Dimethyl Sulfoxide → HCID 11008421, compound

Participants

Reaction Steps

In a 250 mL flask with t-BuOK (11.95 g, 0.11 mol) inside, dry DMSO 50 mL was added under argon to give a colorless solution. Then at room temperature, cis-3-(benzyloxymethyl)cyclobutyl-tosylate (12.3 g, 35.5 mmol) was added very slowly to the previous flask. The reaction mixture was left stirring at room temperature for 4 hr, after which time quench the reaction by adding H2O 200 mL slowly, followed by the addition of 100 mL Et2O. The separated water phase was re-extracted with Et2O three times and the combined organic phase was washed with H2O four times. The organic phase was dried over MgSO4 and concentrated to dryness to give a light yellow oil which was purified by silica gel flash chromatography (Hexane:EtOAc=9:1) to give 4.45 g (71.9%, Rf=0.59 ((Hexane: EtOAc=9:1)) the desired product. 1H NMR (CDCl3, 600 MHz): δ 2.19-2.21 (d, J=12, 1H), 2.66-2.69 (dd, J=13.2, 4.2, 1H), 3.11-3.14 (m, 1H), 3.50-3.56 (m, 2H), 4.54 (s, 2H), 6.09-6.11 (m, 2H), 7.27-7.35 (m, 5H). 13C NMR (CDCl3, 150 MHz): δ 34.40, 43.72, 73.32, 74.07, 127.75, 127.89, 128.59, 137.16, 138.59. IR (neat) νmax 3257, 2917, 2849, 1739, 1462, 1376, 1241, 967, 746.

Provenance & Evidence