ChemicalBook CAS DataBase List METHYL 2-PYRIDYLACETATE

METHYL 2-PYRIDYLACETATE synthesis

11synthesis methods

Product Name:METHYL 2-PYRIDYLACETATE
CAS Number:1658-42-0
Molecular formula:C8H9NO2
Molecular Weight:151.16

67-56-1

16179-97-8

1658-42-0

The general procedure for the synthesis of methyl 2-pyridylacetate from methanol and 2-pyridylacetic acid hydrochloride was as follows: the target compound was prepared by referring to literature methods. 2.00 g of 2-pyridine acetic acid hydrochloride (11.5 mmol, 1.00 eq.) was added to a round-bottom flask with 14 mL of methanol. The reaction system was cooled to 0 °C and 2.90 mL of trimethylchlorosilane (23.0 mmol, 2.00 eq.) was slowly added dropwise. After the dropwise addition, the reaction mixture was gradually warmed to room temperature and stirred overnight. After completion of the reaction, the solvent was removed by rotary evaporator under reduced pressure. The residual solid was neutralized by slowly adding 40 mL of saturated aqueous sodium bicarbonate solution to the residual solid. Subsequently, the aqueous phase was extracted with dichloromethane (4 x 40 mL), and the organic phase was combined and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to afford the crude product methyl 2-pyridylacetate (1.73 g, 11.47 mmol, quantitative yield) as a clear oil. The structure of the product was confirmed by comparing the spectral data of the compound with data reported in the literature.

67-56-1 Synthesis

67-56-1
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$9.00/25ml

16179-97-8
281 suppliers
$14.00/1g

1658-42-0
180 suppliers
$11.00/1g

Yield:1658-42-0 100%

Reaction Conditions:

Stage #1: methanol;pyridin-2-yl acetic acid hydrochloridewith chloro-trimethyl-silane at 0 - 20;Inert atmosphere;
Stage #2: with sodium hydrogencarbonate in water;

Steps:

Synthesis of ligand L9

S2 was prepared analogously to a published procedure.13 2.00 g S1 (11.5 mmol, 1.00 equiv.) and 14 mL MeOH were added to a round-bottom flask. The solution was cooled to 0 °C, and 2.90 mL TMSCl (23.0 mmol, 2.00 equiv.) were added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The solvent was then removed in vacuo, ant the remaining solid was treated slowly with sat. aq. NaHCO3 (40 mL). The aqueous solution was extracted with CH2Cl2 (4 x 40 mL), and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed in vacuo. The crude product (S2) was isolated as a clear oil (1.73 g, 11.47 mmol, quant.). The spectral data of the compound were compared with the published ones.13

References:

Podhajsky, Susanne M.;Iwai, Yasumasa;Cook-Sneathen, Amanda;Sigman, Matthew S. [Tetrahedron,2011,vol. 67,# 24,p. 4435 - 4441] Location in patent:supporting information; experimental part

16179-97-8
281 suppliers
$14.00/1g

1658-42-0
180 suppliers
$11.00/1g

References