Trimethyltin chloride → HCID 178477785, compound

HRID 1942852Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]2[S:6][CH:7]=[CH:8][C:2]1=2.C([Li])(C)(C)C.[CH3:14][Sn:15](Cl)([CH3:17])[CH3:16]>C1COCC1.CCCCC.C(OCC)C>[CH3:14][Sn:15]([CH3:17])([CH3:16])[SH:1]1[CH:5]=[C:4]([Sn:15]([CH3:17])([CH3:16])[CH3:14])[C:3]2[S:6][CH:7]=[CH:8][C:2]1=2

Participants

Conditions

Temperature: -78 °C

Procedure

1 g (7.1 mmol) thieno[3,2-b]thiophene are dissolved in 40 ml anhydrous THF under argon and cooled to −78° C. 11 ml (17.6 mmol) of a 1.6 M tert-butyllithium solution in pentane are added slowly. The mixture is stirred for 2 hours at −78° C., then 4 g (20 mmol) trimethyltin chloride are added as solid. The solution is warmed to room temperature and, stirred for one hour. The solution is diluted with 100 ml diethylether, extracted with aqueous sodium bicarbonate solution, dried and evaporated. The residue is crystallized from acetonitrile at −20° C. to yield 1.9 g (58%) of colorless crystals. Mp=130° C., MS (FD, 8 kV) m/z=465.4 g/mol—calculated: 465.9 g/mol for C12H20S2Sn2; 1H-NMR (300 MHz, CD2 Cl2, RT): δ 7.28 (s, 2H), δ 0.41 (s, 2H); 13C-NMR (75 MHz, CD2Cl2, RT): δ 148.0, 142.0, 16.6, −8.0; elemental analysis: found 30.91%, 4,48% H, 13.61% S—calculated: 30.94% C, 4.33% H, 13.77% S.

Workup

temperatureThe solution is warmed to room temperature
stirringstirred for one hour
extractionextracted with aqueous sodium bicarbonate solution
customdried
customevaporated
customThe residue is crystallized from acetonitrile at −20° C.

Sources & evidence

ORD record: ord-582809035d924f2e8a60176631a3a4f1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389670B2

Reaction notes

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