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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 61893Generated: October 26, 2026

Ethyl isobutyrate → 2-(6-Methoxy-pyridin-2-yl)-2-methyl-propionic acid ethyl ester

https://huagongshe.com/reaction/61893

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl isobutyrateHCID 7342—
ReactantTetrahydrofuranHCID 8028—
Reactant2-Bromo-6-methoxypyridineHCID 256810—
ReactantLithium HexamethyldisilazideHCID 2733832—
CatalystTris(1,1-dimethylethyl)phosphineHCID 83681—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
Product2-(6-Methoxy-pyridin-2-yl)-2-methyl-propionic acid ethyl esterHCID 6683492564.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

2-Bromo-6-methoxypyridine (7.0 g), ethyl isobutyrate (4.75 g), tri t-butylphosphine (300 mg) and Pd2(dba)3 (680 mg) were dissolved in toluene (200 ml) under nitrogen atmosphere, added with THF solution of LiHMDS (1.6 M, 24 ml), and the mixture was stirred at 100° C. for 6 hrs. The reaction mixture was diluted with ethyl acetate (300 ml), and washed three times with 15% brine (200 ml). The organic layer was concentrated under reduced pressure and the resulting residues were purified by silica gel column (n-hexane/ethyl acetate=4/1) to obtain the title compound (5.353 g, yield 60%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440922B2
Source datasetuspto-grants-2016_09
ORD IDord-e6f1d85672d846248de4662bd3f783e2
Source noteuspto-grants-2016_09