Tetrahydrofuran → HCID 131734107, compound

HRID 715911Notes

Reaction equation

HRID 715911 reaction equation
[Li]CCCC.C1COCC1.[S:11]1[CH:15]=[CH:14][C:13]2[CH:16]=[C:17]3[C:25](=[CH:26][C:12]1=2)[CH:24]=[C:23]1[C:19]([S:20][CH:21]=[CH:22]1)=[CH:18]3.[CH3:27][Sn:28](Cl)([CH3:30])[CH3:29]>O>[CH3:27][Sn:28]([CH3:30])([CH3:29])[C:15]1[S:11][C:12]2[CH:26]=[C:25]3[C:17](=[CH:16][C:13]=2[CH:14]=1)[CH:18]=[C:19]1[S:20][C:21]([Sn:28]([CH3:30])([CH3:29])[CH3:27])=[CH:22][C:23]1=[CH:24]3

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14016Trimethyltin chlorideHCID 59522962HCID 59522962, compoundHCID 178418339Butyllithium

Product 1

HCID 131734107HCID 131734107, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere, n-BuLi (1.57N hexane solution, 5.7 ml, 8.9 mmol) was slowly added to an anhydrous THF (80 mL) solution of naphtho[2,3-b:6,7-b′]dithiophene (a compound of formula (2)) (675 mg, 2.8 mmol) at −78° C. The reaction solution was heated and refluxed. After the reaction for 1.5 hours, the reaction solution was cooled to −78° C. To the reaction solution, trimethyltin chloride (2.24 g, 11.2 mmol) was added. After the mixture was stirred at room temperature for 11 hours, and water (100 mL) was added thereto. The resultant mixture was separated into phases. The water layer was extracted with methylene chloride (100 mL×3). The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The resultant residue was recrystallized with acetone to obtain 2,7-bis(trimethylstannyl)naphtho[2,3-b:6,7-b′]dithiophene (861 mg, yield 54%) as a yellow solid substance.

Workup

  1. temperatureThe reaction solution was heated
  2. temperaturerefluxed
  3. customAfter the reaction for 1.5 hours
  4. customThe resultant mixture was separated into phases
  5. extractionThe water layer was extracted with methylene chloride (100 mL×3)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was recrystallized with acetone

Sources & evidence

ORD record
ord-9804d30a549940a69b3824b4bfb2b1fb
Source dataset
uspto-grants-2015_11
Patent number
US09187493B2

Reaction notes

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