Ethanol → HCID 86686197, compound

HRID 1021261Notes

Reaction equation

HRID 1021261 reaction equation
[C:1]([Si:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[C:17][Si](C)(C)C)[C:11]=1[F:22])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].CCO.C(=O)([O-])[O-].[K+].[K+].O>C(Cl)(Cl)Cl>[C:1]([Si:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[CH:17])[C:11]=1[F:22])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 11430Potassium CarbonateHCID 86686225HCID 86686225, compound

Product 1

HCID 86686197HCID 86686197, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

tert-Butyl({2-fluoro-3-[(trimethylsilyl)ethynyl]benzyl}oxy)dimethylsilane (4.13 g) was mixed with EtOH (61 ml), and potassium carbonate (847 mg) was added thereto, followed by stirring at room temperature for 1 hour. Water and CHCl3 were added to the reaction mixture at 0° C., and the organic layer was washed with water and saturated brine, dried over Na2SO4, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl[(3-ethynyl-2-fluorobenzyl)oxy]dimethylsilane (3.19 g).

Workup

  1. additionwas added
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-fd5f48c4b88246f28d70808b75a7bc3d
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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