Water → HCID 58434869, compound

HRID 2195092Notes

Reaction equation

HRID 2195092 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

Preparation of 4,8-didodecyl-2,6-Bis-trimethylstannylbenzo[1, 2-1):4,5-b′]dithiophene. 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, 18 H). 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-7ccfe5d6800f43f5a91234857bd77d56
Source dataset
uspto-grants-2012_12
Patent number
US08334456B2

Reaction notes

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