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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1600913Generated: October 28, 2026

Benzoic Acid → (2R)-2-Benzoyloxy-4-(3-pyridyl)-1-butyl para-toluenesulfonate

https://huagongshe.com/reaction/1600913

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzoic AcidHCID 243—
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
Reactant(2S)-2-hydroxy-4-(3-pyridyl)-1-butyl para-toluenesulfonateHCID 57064601—
SolventTetrahydrofuranHCID 8028—
Product(2R)-2-Benzoyloxy-4-(3-pyridyl)-1-butyl para-toluenesulfonateHCID 5378075964.7%

Reaction Steps

Diethyl azodicarboxylate (0.61 ml) was added to a solution of (2S)-2-hydroxy-4-(3-pyridyl)-1-butyl para-toluenesulfonate (1.4 g), triphenylphosphine (1.31 g) and benzoic acid (0.61 g) in tetrahydrofuran (30 ml) at 0° C. and the resulting solution stirred for 1 hour. The mixture was concentrated under reduced pressure and the residue obtained purified by column chromatography over silica eluting with diethyl ether to give the sub-title compound as a white solid (1.2 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05977105
Source datasetuspto-grants-1999_11
ORD IDord-85da5f34290048f1869a59e7925a0a7e
Source noteuspto-grants-1999_11