1,1,1-Trifluoro-N-phenylmethanesulfonamide → 5,5-Dimethyl-1-cyclopenten-1-yl 1,1,1-trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,2-dimethylcyclopentanone B.1 (available from ChemSampCo) (3.00 g, 26.75 mmol) in THF (100 mL), was slowly added LDA (14.7 mL, 2.0 M, in heptane) at −78° C. The resulting mixture was stirred at −78° C. for 1 hour. A solution of N-phenyltriflamide (10.00 g, 28.00 mmol) was added to the mixture at −78° C., and stirring was continued at 0° C. for 2 hours and then at room temperature overnight. The reaction mixture was extracted with hexane (80×2 mL). The organic layer was washed with saturated Na2CO3 (30 mL), brine (20 mL), and dried with MgSO4. The solvent was removed, and the residue was purified by CombiFlash® chromatography (eluent was EtOAc and hexane) to give B.2. 1H NMR (CDCl3) δ 1.16 (s, 6H), 1.86 (t, J=7.1 Hz, 2H), 2.36 (t, J=7.1 Hz, 2H), 5.56 (m, 1H).

Provenance & Evidence