Chlorotrimethylsilane → HCID 555278, compound

HRID 1454352Notes

Reaction equation

HRID 1454352 reaction equation
C([Li])CCC.[C:6]1([OH:17])[C:15]([F:16])=[C:13]([F:14])[C:11]([F:12])=[C:9]([F:10])[C:7]=1[F:8].Cl[Si:19]([CH3:22])([CH3:21])[CH3:20]>CCCCCC>[C:6]1([O:17][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:7]([F:8])=[C:9]([F:10])[C:11]([F:12])=[C:13]([F:14])[C:15]=1[F:16]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 13041PentafluorophenolHCID 178418339Butyllithium2×

Product 1

HCID 555278HCID 555278, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

n-Butyllithium (9.75 mL, 22.39 mmol, 2.5 M in hexane) was added dropwise, at 0° C., to a 200 mL hexane solution of C6F5OH (4.08 g, 22.17 mmol). After the addition of n-butyllithium was complete, the reaction mixture was allowed to warm to room temperature. Chlorotrimethylsilane (2.65 g, 24.39 mmol) was added to the reaction at −40° C. After slowly warming to room temperature, the reaction was refluxed for 19 hours. Isolation of the crude product was achieved by ether extraction. The organic was washed with ammonium chloride, water, brine, and dried over sodium sulfate. Solvent was removed in vacuo to yield 4.0 g of crude product. The resulting liquid was purified by vacuum distillation to give 3.4 g (60%) of a colorless liquid. 1H NMR (C6D6): δ 0.081 (br. s).

Workup

  1. temperatureAfter slowly warming to room temperature
  2. temperaturethe reaction was refluxed for 19 hours
  3. extractionIsolation of the crude product was achieved by ether extraction
  4. washThe organic was washed with ammonium chloride, water, brine
  5. dry with materialdried over sodium sulfate
  6. customSolvent was removed in vacuo
  7. customto yield 4.0 g of crude product
  8. distillationThe resulting liquid was purified by vacuum distillation

Sources & evidence

ORD record
ord-5ab4670352d146ad9188e6a7ab9faef6
Source dataset
uspto-grants-2009_01
Patent number
US07479529B2

Reaction notes

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