N,N,N',N'-Tetramethylethylenediamine → HCID 57864578, compound

HRID 1971859Notes

Reaction equation

HRID 1971859 reaction equation
[Li]CCCC.[Se:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[Se:12][CH:13]=[CH:14][CH:15]=1.CN(CCN(C)C)C.[CH3:24][Sn:25](Cl)([CH3:27])[CH3:26]>C1COCC1.CC#N>[CH3:24][Sn:25]([CH3:27])([CH3:26])[C:10]1[Se:6][C:7]([C:11]2[Se:12][C:13]([Sn:25]([CH3:27])([CH3:26])[CH3:24])=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 14016Trimethyltin chlorideHCID 5141513HCID 5141513, compoundHCID 178418339Butyllithium2×

Product 1

HCID 57864578HCID 57864578, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
17 °C

Procedure

A solution of BuLi in hexanes (10.6 ml of a 1.6 M solution, 17 mmol) is added dropwise to a cooled (−78° C.) solution of 2,2′-biselenophene (2.00 g, 7.7 mmol) in THF (50 ml) and TMEDA (1.98 g, 17 mmol). On addition of the BuLi an immediate colour change is observed (dark red). After stirring for 20 min, the reaction mixture appeared dark yellow. The mixture is stirred for 6 h allowing to warm to 16-18° C. While warming the reaction mixture changed appearance to a green suspension. The reaction mixture is then cooled to −70° C. Trimethylstannyl chloride (3.38 g, 17 mmol) is added as a solid to the reaction mixture. After 10 min, the reaction mixture appeared brown. The reaction mixture is allowed to warm to room temperature overnight. The reaction is quenched with water (100 mL) and the mixture stirred for 1 h. Ethylacetate (100 mL) is added to the mixture. The layers are separated. The combined organic extracts are washed with water, brine and then dried (Na2SO4). After filtration the crude product is concentrated to yield a brown oil. MeCN is added and the mixture is stirred for 5 min. The mixture is recrystallized three times from acetonitrile. The material is used without further purification. MS (EI) 588 (M+).

Workup

  1. stirringThe mixture is stirred for 6 h
  2. temperatureWhile warming the reaction mixture
  3. temperatureThe reaction mixture is then cooled to −70° C
  4. waitAfter 10 min
  5. temperatureto warm to room temperature overnight
  6. customThe reaction is quenched with water (100 mL)
  7. stirringthe mixture stirred for 1 h
  8. additionEthylacetate (100 mL) is added to the mixture
  9. customThe layers are separated
  10. washThe combined organic extracts are washed with water, brine
  11. dry with materialdried (Na2SO4)
  12. filtrationAfter filtration the crude product
  13. concentrationis concentrated
  14. customto yield a brown oil
  15. stirringthe mixture is stirred for 5 min
  16. customThe mixture is recrystallized three times from acetonitrile
  17. customThe material is used without further purification

Sources & evidence

ORD record
ord-e41f763cc1d04822a456697eb1eddb01
Source dataset
uspto-grants-2013_04
Patent number
US08431682B2

Reaction notes

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