Water → HCID 89157144, compound

HRID 590904Notes

Reaction equation

HRID 590904 reaction equation
[CH2:1]([CH:5]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:6][O:7][C:8]1[C:17]2[CH:16]=[C:15]3[S:18][CH:19]=[CH:20][C:14]3=[C:13]([O:21][CH2:22][CH:23]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:12]=2[CH:11]=[C:10]2[S:34][CH:35]=[CH:36][C:9]=12)[CH2:2][CH2:3][CH3:4].C([Li])CCC.[Sn:48](Cl)([CH3:51])([CH3:50])[CH3:49].O>C1COCC1.CCCCCC>[CH2:1]([CH:5]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:6][O:7][C:8]1[C:9]2[CH:36]=[C:35]([Sn:48]([CH3:51])([CH3:50])[CH3:49])[S:34][C:10]=2[CH:11]=[C:12]2[C:17]=1[CH:16]=[C:15]1[C:14](=[C:13]2[O:21][CH2:22][CH:23]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:20]=[C:19]([Sn:48]([CH3:51])([CH3:50])[CH3:49])[S:18]1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 70981382HCID 70981382, compoundHCID 178418339Butyllithium

Product 1

HCID 89157144HCID 89157144, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution in which 0.48 g of 4,9-bis(2-butyloctyloxy)-1,6-dithia-dicyclopenta[b,g]-naphthalene (0.78 mmol) prepared in Example 2 was dissolved in 20 mL of dry THF was cooled to −78° C., 1.9 mL of n-butyllithium (2.5M solution in hexane, 4.72 mmol) was added thereto. The reaction solution was stirred for 30 minutes and then stirred again at room temperature for 30 minutes. The reaction solution was cooled to −78° C. again, and 4.72 mL of Me3SnCl (1M solution in hexane, 4.72 mmol) was slowly dropped therein. After the reaction solution was stirred again for 30 minutes, a temperature of the reaction solution was raised to room temperature, and the reaction solution was stirred for 12 hours. Water was added to the reaction solution, and a solvent layer was separated. The separated solvent layer was condensed, diluted with hexane, washed with distilled water, dried over Na2SO4, followed by filtering. Then, the obtained filtrate was condensed. The condensed filtrate was recrystallized using isopropanol, thereby obtaining 0.5 g of the title compound (68%) as a yellow solid.

Workup

  1. stirringstirred again at room temperature for 30 minutes
  2. temperatureThe reaction solution was cooled to −78° C. again
  3. stirringAfter the reaction solution was stirred again for 30 minutes
  4. temperaturea temperature of the reaction solution was raised to room temperature
  5. stirringthe reaction solution was stirred for 12 hours
  6. customa solvent layer was separated
  7. customcondensed
  8. washwashed with distilled water
  9. dry with materialdried over Na2SO4
  10. filtrationby filtering
  11. customcondensed
  12. customThe condensed filtrate was recrystallized

Sources & evidence

ORD record
ord-555ecff687d34fbc886ac2db8c79a22b
Source dataset
uspto-grants-2016_01
Patent number
US09236573B2

Reaction notes

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