Methyl iodide → HCID 10774268, compound

Participants

Reaction Steps

To a mixture of ketopinic acid 6a 0.182 g (1 mmol) and K2CO3 1.1 g (8 mmol) stirred in DMF 10 ml was added MeI 0.125 ml (0.284 g, 2 mmol). The reaction mixture was allowed to stir for 18 hrs at ambient temperature. The reaction mixture was dissolved in water 80 ml and extracted with 3×30 ml portions of diethyl ether. The organic phase was washed with NaHCO3 saturated solution, dried over MgSO4 and concentrated in vacuo to give yellow oil 0.184 g (94%). 1H NMR (300 MHz, CDCl3) δ ppm 3.75 (s, 3H), 2.53 (ddd, J=18.29, 3.7 Hz, 1H), 2.36 (ddd, J=14.99, 11.82, 3.99 Hz, 1H), 2.10 (t, J=4.4 Hz, 1H), 2.02 (m, 1H), 1.92-1.98 (d, J=18.40 Hz, 1H), 1.79 (ddd, J=14.16, 9.35, 4.95 Hz, 1H), 1.41 (ddd, J=12.65, 9.49, 4.26 Hz, 1H), 1.15 (s, 3H), 1.07 (s, 3H). Exact mass calculated for C11H16O3 m/e 196.11. found 196.22.

Provenance & Evidence