Trimethyltin chloride → HCID 58204743, compound

HRID 1498120Notes

Reaction equation

[Si:1]([O:8][C:9]([CH3:18])([CH3:17])[CH2:10][N:11]1[CH:15]=[C:14](I)[N:13]=[CH:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Mg]Br)C.[CH3:23][Sn:24](Cl)([CH3:26])[CH3:25]>C(Cl)Cl>[Si:1]([O:8][C:9]([CH3:18])([CH3:17])[CH2:10][N:11]1[CH:15]=[C:14]([Sn:24]([CH3:26])([CH3:25])[CH3:23])[N:13]=[CH:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 10 °C

Procedure

To a mixture of 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-iodo-1H-imidazole in DCM was added ethylmagnesium bromide at −78° C. The temperature of the mixture was allowed to warm up to about 10° C. slowly and cooled again. Trimethyltin chloride was added dropwise at −78° C. After the addition, the temperature was allowed to slowly warm up to room temperature. The reaction mixture was pouted into saturate NH4Cl solution, then extracted with DCM. The organic phase was washed with water twice, dried over anhydrous Na2SO4, and concentrated to give 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-(trimethylstannyl)-1H-imidazole (Yield=74%). LC-MS: m/z=419[M+H+]1H NMR (CDCl3, 400 MHz): δ 7.63 (s, 1 H), 7.00 (s, 1 H), 3.79 (s, 2 H), 1.22-1.19 (s, 6 H), 0.86 (s, 9 H), 0.27 (s, 6 H), 0.02 (s, 6 H)

Workup

temperaturecooled again
additionAfter the addition
temperatureto slowly warm up to room temperature
concentrationinto saturate NH4Cl solution
extractionextracted with DCM
washThe organic phase was washed with water twice
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-bc7a4b7bb0fe454996866af3c2a98b82
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198918B2

Reaction notes

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