Lithium Hydroxide → Methyl 4-iodopicolinate

Participants

Reaction Steps

To a solution of ester 11a′ (Z=ethyl, n=1; 25 mg, 0.07 mmol) in dioxane/water (3:1, 3 mL), LiOH (15.0 mg, 0.35 mmol) solid was added. The resulting mixture was stirred vigorously at rt for 3 h. The organic solvent was removed under reduced pressure, and the residue was dissolved in H2O (10 mL), acidified with aq. HCl (1.0 M) to pH value 3-4, and then extracted with DCM (3×15 mL). The combined organic layers were dried over MgSO4, the solvent was removed, and the residue was dried in high vacuum to afford the desired acid 11b′ (R=OEt, n=1; 22 mg, 95%) as colorless oil.

Provenance & Evidence