Lithium diisopropylamide → HCID 86731500, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 4-methylenecyclohexanecarboxylate (2 g, 11.89 mmol) in THF (5 mL) was cooled at −78° C. and then added over a period of 5 min to the LDA solution. The resulted reaction mixture was stirred at −78° C. for 0.5 h. Then a solution of N-fluorobenzenesulfonamide (4.2 g, 13.32 mmol) in THF (25 mL) was added dropwise over a period of 5 min. The reaction mixture was stirred in the cool bath and allowed to slowly reach rt. After 18 h, it was diluted with EtOAc, washed with a saturated aqueous solution of NH4Cl (2×), water and brine. The organic layer was dried over MgSO4, concentrated and purified on a 25 g silica gel cartridge to afford the product as a liquid (1.97 g, 81% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 4.74 (t, J=1.6 Hz, 2H), 4.25 (q, J=7.2 Hz, 2H), 2.51-2.35 (m, 2H), 2.31-2.22 (m, 2H), 2.18-2.06 (m, 2H), 2.05-1.80 (m, 2H), 1.37-1.24 (m, 3H).

Provenance & Evidence