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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1186353Generated: November 3, 2026

Toluene → HCID 63220265, compound

https://huagongshe.com/reaction/1186353

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
Reactant3-BromopyridineHCID 12286—
ReactantTetrahydro-4H-pyran-4-oneHCID 121599—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
SolventHexaneHCID 8058—
ProductHCID 63220265HCID 6322026530%

Reaction Steps

According to Reference Example 8-23, by use of toluene (3.3+1.1 mL), n-butyllithium (a 2.77 mol/L solution in hexane, 1.24 mL, 2.28 mmol), 3-bromopyridine (300 μL, 3.12 mmol), tetrahydrofuran (1.1 mL) and tetrahydropyran-4-one (345 μL, 3.74 mmol), the mixture was stirred and reacted at 0° C. for 2 hours. Then, purification by silica gel column chromatography (chloroform/methanol=19/1) was performed to give 4-hydroxy-4-(pyridin-3-yl)tetrahydropyran (Compound DF) (167 mg, yield: 30%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08673908B2
Source datasetuspto-grants-2014_03
ORD IDord-47176577def84615831e8c648cfd3cc2
Source noteuspto-grants-2014_03