Tributyltin Chloride → 1-methyl-5-(tributylstannyl)-1H-1,2,3-triazole

HRID 355371Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[N:3]1.C([Li])CCC.[CH2:12]([Sn:16]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])Cl)[CH2:13][CH2:14][CH3:15]>O1CCCC1.[Cl-].[Na+].O>[CH3:1][N:2]1[C:6]([Sn:16]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:5][N:4]=[N:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-methyl-1H-[1,2,3]triazole (350 mg) in dry tetrahydrofuran (5.0 ml) was added dropwise under nitrogen to a stirred, cooled (-78° C.) solution of n-butyl lithium (2.81 ml of 1.6M solution in hexanes) in dry tetrahydrofuran (10 ml). After 1 hour tributylchlorostannane (1.46 g) was added. The reaction was maintained at -78° C. for 30 min. and then allowed to warm to room temperature over 2 hours. The reaction mixture was diluted with brine (10 ml) and extracted into ethyl acetate (50 ml). The organic layer was separated, washed with brine (50 ml), dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue was purified by flash column chromatography (20% ethyl acetate/n-hexane), to give 1-methyl-5-tributylstannanyl-1H-[1,2,3]triazole as a yellow oil (1.03 g). 1H NMR (360 MHz,CDCl3) δ 0.87 (9H, m), 1.15 (6H, m), 1.28 (6H, m), 1.36 (6H, m), 4.02 (3H, s), 7.60 (1H, s); MS m/z CI+ 372 (M+H+).

Workup

temperatureto warm to room temperature over 2 hours
extractionextracted into ethyl acetate (50 ml)
customThe organic layer was separated
washwashed with brine (50 ml)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent removed under reduced pressure
customThe residue was purified by flash column chromatography (20% ethyl acetate/n-hexane)

Sources & evidence

ORD record: ord-f9792f51fe524687b2d64ce493244239
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05830892

Reaction notes

Loading…