ChemicalBook CAS DataBase List METHYL 2-HYDROXY-2-METHYL-3-OXOBUTYRATE

METHYL 2-HYDROXY-2-METHYL-3-OXOBUTYRATE synthesis

5synthesis methods

Product Name:METHYL 2-HYDROXY-2-METHYL-3-OXOBUTYRATE
CAS Number:72450-34-1
Molecular formula:C6H10O4
Molecular Weight:146.14

17094-21-2
28 suppliers
$110.00/250mg

72450-34-1
23 suppliers
$183.00/1g

Yield:72450-34-1 95%

Reaction Conditions:

with samarium (III) iodide;iodine in tetrahydrofuran;water at 25; for 8 h;Catalytic behavior;Mechanism;Green chemistry;Reagent/catalyst;Solvent;

Steps:

General Procedure for I2-catalyzed direct α-hydroxylation of β-dicarbonyl compounds.

A mixture of the β-dicarbonyl compounds (2 mmol), I₂ (0.02-0.04 mmol, 1-2 mol%), and SmI₃ (0.1mmol, 5 mol%) in THF (10 mL) and H₂O (2 mL) were stirred at 25 °C under air for the givent imes. Upon completion of the reaction (detected by TLC), the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:10~1:5) to provide the corresponding products (See below for characterization data of the products) .Methyl 2-hydroxy-2-methyl-3-oxobutanoate (2a)1. Colorless oil, 277 mg, 95%. ¹H NMR (400 MHz, CDCl₃) δ 4.22 (s, 1H), 3.77 (s, 3H), 2.26 (s, 3H), 1.57 (s, 3H); ¹³C NMR (100 MHz, CDCl₃)δ 205.0, 171.6, 81.1, 53.4, 24.3, 22.0. ESI (m/z): 147.1 (M + H)⁺.

References:

Yu, Shun-Ming;Cui, Kai;Lv, Fei;Yang, Zhen-Yu;Yao, Zhu-Jun [Tetrahedron Letters,2016,vol. 57,# 25,p. 2818 - 2821] Location in patent:supporting information