Diethyl Ether → HCID 86688837, compound

HRID 2275391Notes

Reaction equation

HRID 2275391 reaction equation
[CH2:1]([O:3][C:4]1[C:12]2[S:11][CH:10]=[CH:9][C:8]=2[C:7]([O:13][CH2:14][CH3:15])=[C:6]2[S:16][CH:17]=[CH:18][C:5]=12)[CH3:2].C([Li])CCC.CCCCCC.[CH3:30][Sn:31](Cl)([CH3:33])[CH3:32].CCOCC>C1COCC1.CCCCCC.O>[CH2:14]([O:13][C:7]1[C:6]2[S:16][C:17]([Sn:31]([CH3:33])([CH3:32])[CH3:30])=[CH:18][C:5]=2[C:4]([O:3][CH2:1][CH3:2])=[C:12]2[S:11][C:10]([Sn:31]([CH3:33])([CH3:32])[CH3:30])=[CH:9][C:8]=12)[CH3:15]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 14016Trimethyltin chlorideHCID 387771HCID 387771, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 86688837HCID 86688837, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 556 mg (2.0 mmol) of 4,8-diethoxythieno[2,3-f]benzothiophene (26) in 8 ml of dry THF are added dropwise 1.6 ml (4.1 mmol) of 2.5 M n-butyllithium/hexane solution at −78° C. After the mixture has been stirred at −78° C. for 1 h, the cooling bath is removed and the mixture is stirred at room temperature for a further hour. The mixture is cooled to −78° C. and a solution of 4.2 ml (4.2 mmol) of 1.0 M trimethylstannyl chloride in n-hexane is added. The reaction mixture is stirred at −78° C. for another 10 min and then at room temperature for 16 h. 20 ml of ether and 20 ml of water are added and the organic phase is separated. The aqueous phase is extracted with 20 ml of ether, and the organic phases are combined and dried over sodium sulfate. After the solvents have been distilled off, the residue is dried under reduced pressure. The crude product (1.13 g, 94%) is used in the next stage without further purification. 1H NMR (CDCl3): 7.51 ppm (s, 2H), 4.38 (qa, 4H), 1.50 (t, 6H), 0.45 (s. 18H).

Workup

  1. customthe cooling bath is removed
  2. stirringthe mixture is stirred at room temperature for a further hour
  3. temperatureThe mixture is cooled to −78° C.
  4. stirringThe reaction mixture is stirred at −78° C. for another 10 min
  5. waitat room temperature for 16 h
  6. customthe organic phase is separated
  7. extractionThe aqueous phase is extracted with 20 ml of ether
  8. dry with materialdried over sodium sulfate
  9. distillationAfter the solvents have been distilled off
  10. customthe residue is dried under reduced pressure
  11. customThe crude product (1.13 g, 94%) is used in the next stage without further purification

Sources & evidence

ORD record
ord-845b8bc8a9234d47b81f7747c96f7e61
Source dataset
uspto-grants-2015_09
Patent number
US09127020B2

Reaction notes

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