Sodium Chloride → Tetrahydrofuran hexane

HRID 2413823Notes

Reaction equation

HRID 2413823 reaction equation
[Na].C[SiH](Cl)Cl.[Na+].[Cl-].[CH3:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1>>[CH3:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1

Participants

6

Reactant 5

HCID 5234Sodium ChlorideHCID 6376Methyldichlorosilane2×HCID 8028TetrahydrofuranHCID 8058HexaneHCID 5360545Sodium

Product 1

HCID 21883165Tetrahydrofuran hexaneYield 81%

Procedure

In a dry box, a 1 liter three-necked, round-bottomed flask equipped with a stir-bar, a dropping funnel and a reflux condenser was charged with 75.0 g (3.26 mol) of sodium metal. The flask was attached to a Schlenk manifold, evacuated and flushed with nitrogen. THF (70 ml) and hexane (420 ml) were added and the dropping funnel was charged with 150 ml (1.44 mol) of methyldichlorosilane. Methyldichlorosilane was added slowly into the flask over a 3 hour period. The reaction solution turned purple and by the end of the addition was at gentle reflux. The reaction mixture was stirred at room temperature for 2 hours and then heated at reflux for 16 hours. After it had been cooled to room temperature, the reaction mixture (except for the large NaCl crystals) was transferred via a cannula into a heavy-walled glass bottle. The mixture was centrifuged and the clear, colorless supernatant layer transferred by cannula into a 1 liter round-bottomed flask equipped with a stir-bar. Hexane (200 ml) and THF (20 ml) were added to the remaining solids, the mixture was centrifuged again, and the supernatant liquid combined with the first separated supernatant layer. Solvent was removed by trap-to-trap distillation until the volume of the residue was about 100 ml, and the remaining liquid was transferred by cannula into a weighed 250 ml round-bottomed flask. Remaining solvent was removed by trap-to-trap distillation at approximately 0.05 mm Hg at room temperature to give 51.2 g (81%, 1.16 mol) of a cloudy white oil.

Workup

  1. customIn a dry box, a 1 liter three-necked, round-bottomed flask equipped with a stir-bar, a dropping funnel and a reflux condenser
  2. customThe flask was attached to a Schlenk
  3. custommanifold, evacuated
  4. customflushed with nitrogen
  5. additionTHF (70 ml) and hexane (420 ml) were added
  6. additionThe reaction solution turned purple and by the end of the addition
  7. temperatureheated
  8. temperatureat reflux for 16 hours
  9. temperatureAfter it had been cooled to room temperature
  10. customthe clear, colorless supernatant layer transferred by cannula into a 1 liter round-bottomed flask
  11. customequipped with a stir-bar
  12. customSolvent was removed by trap-to-trap
  13. distillationdistillation until the volume of the residue
  14. customthe remaining liquid was transferred by cannula into a weighed 250 ml round-bottomed flask
  15. customRemaining solvent was removed by trap-to-trap
  16. distillationdistillation at approximately 0.05 mm Hg at room temperature

Sources & evidence

ORD record
ord-447ad4c4c7084b06ab7ce43ab002d7b8
Source dataset
uspto-grants-1988_01
Patent number
US04719273

Reaction notes

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