Chlorotrimethylsilane → HCID 86626439, compound

HRID 1259304Notes

Reaction equation

HRID 1259304 reaction equation
C([Li])CCC.C1[CH2:10][O:9]CC1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Si:19]([CH3:22])([CH3:21])[CH3:20])[N:14]=1.Cl[Si:24]([CH3:27])([CH3:26])[CH3:25]>[Cl-].[Na+].O.CCCCCC.O>[CH3:11][O:12][C:13]1[C:18]([CH:10]=[O:9])=[C:17]([Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:16]=[C:15]([Si:19]([CH3:21])([CH3:20])[CH3:22])[N:14]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028Tetrahydrofuran3×HCID 11116670HCID 11116670, compoundHCID 178418339Butyllithium2×

Product 1

HCID 86626439HCID 86626439, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

n-Butyllithium (1.6 M in n-hexane, 2.8 mL, 2.76×1.6 mmol) was added dropwise to a dry THF (6.6 mL) solution of 2-methoxy-6-(trimethylsilyl)pyridine (MTP, 0.500 g, 2.76 mmol) under an argon atmosphere at between −15° C. and 0° C. (this temperature was kept during the reaction) and stirred for 1 hour, and a dry THF (2 mL) solution of FEO (0.434 g, 2.76×1.2 mmol) was then added dropwise and stirred for 1 hour. Subsequently, n-butyllithium (1.6 M in n-hexane, 2.4 mL, 2.76×1.4 mmol) was added dropwise and stirred for 1 hour, and a dry THF (3 mL) solution of chlorotrimethylsilane (697 μL, 2.76×2.0 mmol) was then added dropwise and stirred for 1 hour. The temperature was raised to room temperature, followed by adding water, brine, and n-hexane (50 mL). The organic layer was separated, dried over Na2SO4, filtered, and then concentrated to dryness. The residue was purified by medium pressure silica gel column chromatography (n-hexane), and desired fractions were combined and concentrated to dryness. TMS-MTPC (0.305 g, 1.08 mmol, 39%) was obtained as a colorless transparent liquid.

Workup

  1. customwas kept during the reaction) and
  2. stirringstirred for 1 hour
  3. stirringstirred for 1 hour
  4. stirringstirred for 1 hour
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by medium pressure silica gel column chromatography (n-hexane)
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c01a62f715984b4db73b9bef25dd559e
Source dataset
uspto-grants-2013_06
Patent number
US08466287B2

Reaction notes

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