Methyl acetoacetate → Methyl 3-tetrahydropyrrolyl-2-butenoate

HRID 10834

Reaction equation

HRID 10834 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[NH:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[C:3]([CH3:5])=[CH:2][C:1]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 7757Methyl acetoacetateHCID 31268Pyrrolidine

Product 1

HCID 69630084Methyl 3-tetrahydropyrrolyl-2-butenoateYield 99.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

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%).

Workup

  1. customsolvent was removed
  2. concentrationby concentrating the resulting mixture under a reduced pressure

Sources & evidence

ORD record
ord-8ef35b9c9c5c40bcabb7b408e1cb86f0
Source dataset
uspto-grants-2006_08
Patent number
US07094908B2

Linked notes

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