Tributyltin Chloride → 2,6-Dimethyl-4-(tributylstannyl)pyridine

HRID 1681189Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=1.C([Li])CCC.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>C(OCC)C>[CH3:8][C:6]1[CH:7]=[C:2]([Sn:19]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH2:16][CH2:17][CH3:18])[CH:3]=[C:4]([CH3:9])[N:5]=1

Participants

Conditions

Temperature: -60 °C

Procedure

A 22 L flask was charged with 740 g of 4-bromo-2,6-lutidine and 10.0 L of diethyl ether and cooled to -60° C. in a Dry Ice/acetone bath under nitrogen. A solution of 4.0 moles of n-butyllithium was added dropwise over 1 hour maintaining a temperature below -58° C. to form an orange-yellow precipitate. After continued stirring in the cold for 15 minutes, 1280 g of tributyltin chloride was added over 2 hours at a temperature of -60° to -57° C. to form a solution. The reaction was stirred cold for 45 minutes before it was slowly (2 hours) warmed to 20° C. A portion of Super-Cel (100 g) was added and the reaction mixture was filtered to remove the precipitated lithium chloride. The cake was washed with diethyl ether (2×500 ml). After concentration to dryness a total of 1575 g (99.7% yield) of product was obtained which was used without further purification.

Workup

temperaturemaintaining a temperature below -58° C.
customto form an orange-yellow precipitate
customto form a solution
stirringThe reaction was stirred cold for 45 minutes before it
custom(2 hours)
temperaturewarmed to 20° C
additionA portion of Super-Cel (100 g) was added
filtrationthe reaction mixture was filtered
customto remove the precipitated lithium chloride
washThe cake was washed with diethyl ether (2×500 ml)

Sources & evidence

ORD record: ord-ca1769da5a4c40ffa522e90466013139
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05169853

Reaction notes

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