(Diethylamino)sulfur trifluoride → HCID 118062725, compound

Participants

Reaction Steps

To a solution of ethyl 3-hydroxy-3-methylcyclobutanecarboxylate (500 mg, 3.16 mmol) in DCM (5 mL) was added DAST (0.626 mL, 4.74 mmol) at −78° C. and the reaction mixture was slowly allowed to warm to RT and stir for 3 h. The reaction mixture was diluted with DCM (25 mL), washed with H2O and a saturated aq. solution of NaHCO3, then dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography (12 g REDISEP® column, eluting with 25% EtOAc in hexanes). Fractions containing the product were combined and evaporated to afford Intermediate 288A as a pale yellow liquid (0.2 g, 40% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.08 (q, J=7.0 Hz, 2H), 3.22-3.09 (m, 1H), 2.60-2.53 (m, 1H), 2.37-2.22 (m, 3H), 1.44 (d, J=18 Hz, 3H), 1.22-1.11 (m, 3H).

Provenance & Evidence