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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 10834Generated: October 25, 2026

Methyl acetoacetate → Methyl 3-tetrahydropyrrolyl-2-butenoate

https://huagongshe.com/reaction/10834

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl acetoacetateHCID 7757—
ReactantPyrrolidineHCID 31268—
Catalystp-Toluenesulfonic acid monohydrateHCID 521998—
SolventTolueneHCID 1140—
ProductMethyl 3-tetrahydropyrrolyl-2-butenoateHCID 6963008499.5%

Reaction Conditions

Temperature140 °C

Reaction Steps

Methyl acetoacetate (20 g, 172.23 mmol) was dissolved in 250 mL of toluene, and then pyrrolidine (43 ml, 516.70 mmol) and p-toluenesulfonic acid hydrate (about 100 mg) were added dropwise. After installing a Dean-Stark separator to the reactor, the reaction mixture was refluxed 140° C. for two days, and then solvent was removed by concentrating the resulting mixture under a reduced pressure, thereby to obtain the desired product (29 g, 99%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07094908B2
Source datasetuspto-grants-2006_08
ORD IDord-8ef35b9c9c5c40bcabb7b408e1cb86f0
Source noteuspto-grants-2006_08