methyl 2-methylglycerate synthesis

Yield:19860-56-1 92%

Reaction Conditions:

with potassium permanganate;N-benzyl-N,N,N-triethylammonium chloride in acetone at -2 - 2; for 0.5 h;

Steps:

α,β-Dihydroxy Esters 1b-14b; General Procedure

General procedure: TEBAC (6 mmol) and KMnO₄ (6 mmol) were mixed in acetone (10 mL), and the mixture was stirred at r.t. for 3 h then cooled to 0 °C. A solution of the appropriate enoate 1a-14a (5 mmol) in acetone (2 mL) was added dropwise over 5 min while the internal temperature was kept at 5 °C or below. After completion of the addition, the mixture was stirred for a further 30 min at 0 °C until the enoate was completely consumed (TLC). Sat. aq NaHSO₃ (5 mL) was added in one portion to quench the reaction, and the mixture was filtered through Celite, which was washed with acetone. The filtrate was concentrated on a rotary evaporator and the residue was extracted with EtOAc. The organic phase was dried (Na₂SO₄), filtered, and evaporated to dryness.The crude oily product was purified by column chromatography (silica gel, 25% EtOAc in PE).

References:

Luo, Zhi-Bin;Zhao, Chen;Xie, Jimin;Lu, Hong-Fei [Synthesis,2016,vol. 48,# 21,art. no. SS-2016-H0270-PSP,p. 3696 - 3700]