Tributyltin Chloride → 4-(5-Tributylstannanyl-[1,2,3]triazol-1-yl)-benzonitrile

HRID 1640684Notes

Reaction equation

[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[Li]C(C)(C)C.[Sn:19](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23]>C1COCC1>[CH2:28]([Sn:19]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[C:5]1[N:1]([C:6]2[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=2)[N:2]=[N:3][CH:4]=1)[CH2:29][CH2:30][CH3:31]

Participants

Conditions

Temperature: -78 °C

Procedure

4-[1,2,3]Triazol-1-yl-benzonitrile (0.105 g, 0.6 mmol) and dry THF (6 ml) and a magnetic stirrer were placed in a flask. The flask was flushed with argon and kept under an inert atmosphere and cooled to −78° C. At this temperature, tert-BuLi (0.36 ml, 1.7M, 0.6 mmol) was added dropwise during 1-2 minutes. The mixture was stirred at this temperature for 15 minutes and Bu3SnCl (0.19 g, 0.6 mmol) was added during 1 minute, and the mixture was then allowed to slowly reach RT. The crude mixture was directly purified on silica (heptane:EtOAc 4:1) giving 0.12 g (43%) of the title stannane.

Workup

customThe flask was flushed with argon
customwas then allowed to slowly reach RT
customThe crude mixture was directly purified on silica (heptane:EtOAc 4:1)

Sources & evidence

ORD record: ord-051bbb93984f4f4e82433791b3247235
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114881B2

Reaction notes

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