Water → HCID 58434869, compound

HRID 405040Notes

Reaction equation

HRID 405040 reaction equation
[CH2:1]([C:13]1[C:21]2[S:22][CH:23]=[CH:24][C:20]=2[C:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[C:15]2[S:16][CH:17]=[CH:18][C:14]=12)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C([Li])CCC.[CH3:42][Sn:43](Cl)([CH3:45])[CH3:44].O>O1CCCC1>[CH2:1]([C:13]1[C:21]2[S:22][C:23]([Sn:43]([CH3:45])([CH3:44])[CH3:42])=[CH:24][C:20]=2[C:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[C:15]2[S:16][C:17]([Sn:43]([CH3:45])([CH3:44])[CH3:42])=[CH:18][C:14]=12)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 53375634HCID 53375634, compoundHCID 178418339Butyllithium

Product 1

HCID 58434869HCID 58434869, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,8-didodecylbenzo[1,2-b:4,5-b′]dithiophene (553 mg, 1.05 mmol) in dry tetrahydrofuran (16 mL) was added n-butyllithium (2.5 M in hexane, 0.92 mL, 2.31 mmol) at −78° C. After 1 hour, trimethyltin chloride (488 mg, 2.45 mmol) was added in one portion. The mixture was stirred at room temperature for 2 hours, poured into water and extracted with ether three times. The organic layer was washed with brine and dried over anhydrous MgSO4. Upon evaporating the solvent, a pale yellow oil was obtained which is recrystallized from EtOH to give a white solid (524 mg, yield 58%). 1H NMR (CDCl3, 500 MHz) δ=7.51 (s, 2H), 3.22 (t, J=8.0 Hz, 4H), 1.76-1.91 (m, 4H), 1.36-1.42 (m, 4H), 1.22-1.42 (bs, 32H), 0.91 (t, J=7.0 Hz, 6H), 0.47 (s, 18H). See also, Chem. Mater. 2006, 18, 3237.

Workup

  1. extractionextracted with ether three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customUpon evaporating the solvent
  5. customa pale yellow oil was obtained which
  6. customis recrystallized from EtOH

Sources & evidence

ORD record
ord-66862353469a49f2b430f0a6244afecc
Source dataset
uspto-grants-2014_06
Patent number
US08748739B2

Reaction notes

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