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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2365310Generated: October 28, 2026

Methylparaben → Methyl 4-((5-chloropyridin-3-yl)methoxy)benzoate

https://huagongshe.com/reaction/2365310

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethylparabenHCID 7456—
ReactantTriphenylphosphineHCID 11776—
ReactantDiisopropyl azodicarboxylateHCID 5363146—
Reactant(5-Chloropyridin-3-yl)methanolHCID 25067264—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductMethyl 4-((5-chloropyridin-3-yl)methoxy)benzoateHCID 5962594668.8%

Reaction Conditions

Temperature0 °C

Reaction Steps

DIAD (2.35 mmol, 0.45 mL) was added to an ice-cold solution of methyl 4-hydroxybenzoate 29a (2.35 mmol, 358 mg), (5-chloropyridin-3-yl)methanol 27a (1.57 mmol, 225 mg), and Ph3P (2.35 mmol, 616 mg) in 8 mL of THF. The mixture was stirred at 0° C. for 1 h at room temperature overnight. Water was added and the crude product was purified by flash column chromatography (silica gel, 20% EtOAc/hexanes) to afford 300 mg (68%) of 27b.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08697684B2
Source datasetuspto-grants-2014_04
ORD IDord-182374af7d33411eb693757d5956fec7
Source noteuspto-grants-2014_04