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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1756323Generated: November 3, 2026

Methyl 3-formylbenzoate → 2-[(1RS)-1-Hydroxy-1-(3-methoxycarbonylphenyl)-methyl]-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine

https://huagongshe.com/reaction/1756323

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 3-formylbenzoateHCID 639145—
Reactant2-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl)-pyridineHCID 15661708—
ReactantButyllithiumHCID 178418339—
Product2-[(1RS)-1-Hydroxy-1-(3-methoxycarbonylphenyl)-methyl]-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridineHCID 1566171625.5%

Reaction Steps

Under the conditions of example 1B, 326 mg of 2-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine is reacted with 1.38 ml of n-butyllithium (1.6 molar in hexane) and 181 mg of 3-formylbenzoic acid methyl ester (J. Org. Chem. 31, 1966, 2585), worked up and chromatographed on silica gel with hexane/ethyl acetate 8/2. 105 mg of the title compound is obtained as colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05440044
Source datasetuspto-grants-1995_08
ORD IDord-d2b759214b814d32961a8d26f8576731
Source noteuspto-grants-1995_08