2-Phenyl-1,3-dithiane → HCID 86619319, compound

HRID 1820945

Reaction equation

HRID 1820945 reaction equation
[C:1]1([CH:7]2[S:12][CH2:11][CH2:10][CH2:9][S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][CH2:14][CH2:15][CH2:16][CH3:17].[CH2:18]([Ge:20]([CH2:23][CH3:24])(Cl)Cl)[CH3:19]>C1COCC1.CCCCCC>[CH2:18]([Ge:20]([CH2:23][CH3:24])([C:17]1([C:16]2[CH:6]=[CH:1][CH:2]=[CH:14][CH:15]=2)[S:12][CH2:11][CH2:10][CH2:9][S:8]1)[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[S:8][CH2:9][CH2:10][CH2:11][S:12]1)[CH3:19]

Participants

6

Reactant 3

HCID 215472-Phenyl-1,3-dithianeHCID 83334DichlorodiethylgermaneHCID 178418339Butyllithium

Product 1

HCID 86619319HCID 86619319, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

1.85 g (9.42 mmol) 2 phenyl-1,3-dithian was placed in a dry 50-ml three-necked flask under argon and dissolved in 28 ml anhydrous THF. 3.99 ml 2.36 M BuLi solution in hexane was added dropwise at 0° C. and the reaction solution stirred for 2 h at 0° C. 0.83 mg (3.93 mmol) diethyldichlorogermanium dissolved in 8 ml anhydrous THF was added slowly dropwise at 0° C. to the reaction mixture and then stirred for an additional 2 h at 0° C. To complete the reaction a further solution of 2-phenyl-2-lithium-1,3-dithian (2.36 mmol) was prepared as described above and added dropwise at 0° C. to the reaction solution, which was then stirred for 18 h at 6° C. The reaction was quenched by the addition of 20 ml water and the raw product extracted with diethyl ether (3×30 ml). The combined organic phases were dried with Na2SO4 and the solvent drawn off at the rotary evaporator. The residue was separated off by column chromatography (petroleum ether: ethyl acetate=20:1). 1.42 g (70% of the theoretical value) diethylbis(2-phenyl-1,3-dithian-2-yl)germanium was obtained as colorless solid. DC (petroleum ether: ethyl acetate=20:1): Rf=0.51

Workup

  1. additionwas added slowly dropwise at 0° C. to the reaction mixture
  2. stirringstirred for an additional 2 h at 0° C
  3. customthe reaction a further solution of 2-phenyl-2-lithium-1,3-dithian (2.36 mmol)
  4. customwas prepared
  5. additionadded dropwise at 0° C. to the reaction solution, which
  6. stirringwas then stirred for 18 h at 6° C
  7. customThe reaction was quenched by the addition of 20 ml water
  8. extractionthe raw product extracted with diethyl ether (3×30 ml)
  9. dry with materialThe combined organic phases were dried with Na2SO4
  10. customthe solvent drawn off at the rotary evaporator
  11. customThe residue was separated off by column chromatography (petroleum ether: ethyl acetate=20:1)

Sources & evidence

ORD record
ord-dfa0e26209c041fd990b1fa90cd53abe
Source dataset
uspto-grants-2009_10
Patent number
US07605190B2

Linked notes

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