tert-BUTYL CHLORIDE → methyl 5-tert-butyl-1H-pyrrole-2-carboxylate

HRID 18931

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3].[C:14](Cl)([CH3:17])([CH3:16])[CH3:15]>C(=S)=S>[C:14]([C:7]1[NH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:9][CH:8]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of the methylpyrrole-2-carboxylate (1.0 g, 7.99 mmol) and aluminum trichloride (2.13 g, 16.0 mmol) was dissolved in carbon disulfide (20 mL) and stirred at 50° C. for 1 hour. Tert-butyl chloride (0.740 g, 7.99 mmol) in carbon disulfide (5 mL) was added in one portion and the mixture stirred at room temperature for an additional 20 hours. The reaction mixture was quenched with ice and extracted with dichloromethane. The solvent was removed under vacuum and the resulting solid was washed with cold hexane to afford 0.850 g of the expected methyl 5-tert-butyl-1H-pyrrole-2-carboxylate as a tan solid.

Workup

stirringthe mixture stirred at room temperature for an additional 20 hours
customThe reaction mixture was quenched with ice
extractionextracted with dichloromethane
customThe solvent was removed under vacuum
washthe resulting solid was washed with cold hexane

Sources & evidence

ORD record: ord-da6f722551a4427295029d5676767d32
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741479B2

Linked notes

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