Methyl 3-methoxypropionate

Preparation

In a dry reaction flask, 0.2 mL of Na₂CO₃ (0.05 M aq.) was added to a solution of ethyl acrylate (0.5 mmol) and methanol (2.0 mmol). The resulting reaction mixture was stirred at room temperature for approximately 5 hours until the olefins were completely consumed. The reaction progress was monitored by thin-layer chromatography (TLC). After the reaction was complete, the reaction mixture was extracted three times with ethyl acetate (3 x 5 mL). The combined organic layers were washed with brine (10 mL) and dried over Na₂SO₄. The organic layers were filtered to remove the drying agent, and the resulting organic solvent was concentrated under vacuum. The crude product was purified by silica gel column chromatography (eluent: PE: EtOAc = 8:1) to obtain methyl 3-methoxypropionate.

Chemical Properties

clear colorless liquid

Uses

Methyl 3-methoxypropionate may be employed as acylation reagent for the lipase-catalyzed N-acylation of 1-phenylethanamine. It may be used in the synthesis of poly(2-hydroxylethyl 5-norbornene-2-carboxylate /t-butyl 5-norbornene-2-carboxylate /5-norbornene-2-carboxylic acid /maleic anhydride) resists. Lithographic performance of these resists was studied using ArF stepper.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 544, 1946 DOI: 10.1021/ja01208a003

General Description

Methyl 3-methoxypropionate is an ester.