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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 334053Generated: October 30, 2026

Methyl iodide → 6-(Methoxymethyl)pyridine-2-carboxylic acid

https://huagongshe.com/reaction/334053

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactant6-(Hydroxymethyl)picolinic acidHCID 11789404—
SolventTetrahydrofuranHCID 8028—
SolventEthyl AcetateHCID 8857—
Product6-(Methoxymethyl)pyridine-2-carboxylic acidHCID 45082627—

Reaction Conditions

Temperature0 °C

Reaction Steps

To a stirred solution of 300 mg (1.96 mmol) 6-hydroxymethyl-pyridine-2-carboxylic acid in 20 mL THF was added 188 mg (4.31 mmol) NaH in mineral oil (55%) at 0° C. After gas formation ceased, 310 μL (4.90 mmol) methyl iodide was added dropwise, then the mixture was stirred for 1 h at 0° C. and for 1 h at RT. The reaction mixture was diluted with EtOAc, extracted with water, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08883789B2
Source datasetuspto-grants-2014_11
ORD IDord-6736bc0f0b3840618706e3de867459e5
Source noteuspto-grants-2014_11