Potassium Carbonate → 3-Ethyl-2-hydroxyvaleric acid, 4-methoxybenzyl ester

Participants

Reaction Steps

To 1.2 g (8.2 mmol) of 3-ethyl-2-hydroxyvaleric acid (step A) in 15 mL of dry DMF, 1.4 mL (9.6 mmol) of 4-methoxybenzyl chloride and 1.3 g (9.4 mmol) of K2CO3 were added. After stirring the reaction overnight, it was partitioned between Et2O and water. The aqueous layer was extracted with Et2O. The combined organic layer was washed with water, brine, dried and concentrated. The residue was purified on a flash column using a gradient of 10-30% EtOAc in hexane to obtain 2.1 g of the desired product. 1H NMR (CDCl3) 0.84 (t, 3H), 0.96 (t, 3H), 1.2-1.6 (m, 5H), 2.67 (d, 1H), 3.83 (s, 3H), 4.27 (dd, 1H), 5.17 (ABq, 2H), 6.91(m, 2H), 7.31 (m, 2H).

Provenance & Evidence