2-(2-thienyl)propionic acid synthesis

13synthesis methods

Product Name:2-(2-thienyl)propionic acid
CAS Number:54955-39-4
Molecular formula:C7H8O2S
Molecular Weight:156.2

2-Thiopheneacetic acid, α-methyl-, ethyl ester

63476-16-4
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54955-39-4
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Yield:54955-39-4 100%

Reaction Conditions:

with lithium hydroxide monohydrate;water in methanol at 20; for 3 h;

Steps:

4 2-(Thiophen-2 I)propanoic acid

To a solution of ethyl 2-(thiophen-2-yl)propanoate (5.9 g, 32.39 mmol) in methanol (40 mL) and water (15 mL) was added lithium hydroxide monohydrate (2.0 g, 48.4 mmol) and the reaction mixture stirred at RT for 3 H. The reaction mixture was concentrated in vacuo to approximately volume and the residue extracted with EtOAc. The organic fractions were discarded and the aqueous layer was acidified to ~ pH 3 with IN HC1 and extracted with EtOAc. The combined organic fractions were washed with brine, dried (MgS0₄) and concentrated in vacuo to yield the title compound as a yellow oil (5.0 g, 100%). NMR (400 MHz, d₆-DMSO) δ 7.26 (1H, dd, J - 5.2, 1.6 Hz), 6.89 (1H, dd, J = 5.1, 3.5 Hz), 6.87-6.80 (1H, m), 3.74 (1H, q, J = 7.0 Hz), 1.35 (3H, d, J = 7.0 Hz).

References:

WO2019/87146,2019,A1 Location in patent:Page/Page column 28