Diethyl Ether → 2-{2-Chloro-1-[(triisopropylsilyl)oxy]ethenyl}pyridine

HRID 23702Notes

Reaction equation

HRID 23702 reaction equation
[CH:1]([Si:4]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[CH2:7])([CH3:3])[CH3:2].C1C(=O)N([Cl:27])C(=O)C1.CCOCC>C1COCC1>[Cl:27][CH:7]=[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[O:5][Si:4]([CH:1]([CH3:2])[CH3:3])([CH:14]([CH3:16])[CH3:15])[CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 31398ChlorosuccinimideHCID 225632222-(1-((Triisopropylsilyl)oxy)vinyl)pyridine

Product 1

HCID 739919382-{2-Chloro-1-[(triisopropylsilyl)oxy]ethenyl}pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 2-{1-[(triisopropylsilyl)oxy]vinyl}pyridine (131.5 g, assumed 0.413 mmol) is placed in a 2 L, 1N round bottom flask and dissolved in anhydrous THF (Aldrich Sure Seal, 0.6 L). The flask is equipped with a reflux condenser and the apparatus is placed under nitrogen. NCS (60.66 g, 0.454 mol, 1.1 eq.) is added and the mixture is heated to reflux and maintained at reflux for 2 hours. The reaction mixture is cooled to room temperature, poured into a 4 L separatory funnel containing ether (1.5 L), and is washed with saturated aq. NaHCO3 (2×0.7 L). The organic phase is separated, dried (Na2SO4), and concentrated in vacuo affords the target (117.5 g, 91%) as a yellow-orange oil. The crude material is not further purified, but is immediately carried into the next step.

Workup

  1. customThe flask is equipped with a reflux condenser
  2. temperaturethe mixture is heated
  3. temperatureto reflux
  4. temperaturemaintained
  5. temperatureat reflux for 2 hours
  6. additionpoured into a 4 L separatory funnel
  7. washis washed with saturated aq. NaHCO3 (2×0.7 L)
  8. customThe organic phase is separated
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customaffords the target (117.5 g, 91%) as a yellow-orange oil

Sources & evidence

ORD record
ord-90fd900c96b54f749915c8ac40938200
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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