Dichloromethane → HCID 178472502, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl cis-4-hydroxycyclohexanecarboxylate (4.30 g, 25.0 mmol), p-toluenesulfonyl chloride (7.14 g, 37.4 mmol) and DCM (100 mL, 2000 mmol) was added triethylamine (6.96 mL, 49.9 mmol) at rt. The mixture was stirred at 25° C. overnight. The solution was transferred to a separatory funnel, washed with 2 M HCl to remove base, then washed with sat. NaHCO3. The organic layer was dry-loaded onto silica gel for column chromatography, eluting with 10-20% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ=1.16 (t, J=7.2 Hz, 3H), 1.52-1.67 (m, 8H), 2.31-2.40 (m, 1H), 2.42 (s, 3H), 4.05 (q, J=7.1 Hz, 2H), 4.66 (br. s., 1H), 7.47 (m, J=7.8 Hz, 2H), 7.80 (m, J=8.3 Hz, 2H).

Provenance & Evidence