1-Methylpyrrole → 1-methyl-2-(tributylstannyl)-1H-pyrrole

HRID 356601Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.C([Li])CCC.CN(C)CCN(C)C.[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[Sn:24]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: -35 °C

Procedure

1-Methylpyrrole (0.065 g) was added to a cooled (-35° C.), stirred solution of butyllithium (2.5M, 0.32 mL) in dry THF (5 mL). N,N,N',N'-Tetramethylethylenediamine (0.090 g) was then added and the mixture was stirred for 90 min at -10° to -15° C. Tributyltin chloride (0.26 g) was then slowly added, and the mixture was allowed to warm to room temperature and stirred for 15 min. The solvent was evaporated to provide (1-methylpyrrol-2-yl)tributyltin, suitable for use in the next reaction.

Workup

temperatureto warm to room temperature
stirringstirred for 15 min
customThe solvent was evaporated

Sources & evidence

ORD record: ord-e9bf0c21e07d44cbbf5174530827dcd7
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05837704

Reaction notes

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