Trimethylsilane → {5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

HRID 1038605Notes

Reaction equation

HRID 1038605 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:9]([O:18]CC2C=CC(OC)=CC=2)=[CH:8][N:7]=1)(=[O:3])[CH3:2].C[SiH](C)C.FC(F)(F)C([O-])=O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si:14]([CH3:15])([CH3:17])[CH3:16])[C:9]([OH:18])=[CH:8][N:7]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 70435TrimethylsilaneHCID 84468TrifluoroacetateHCID 516892Sodium BicarbonateHCID 57423117{5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

Product 1

HCID 57423119{5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetateYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-((4-Methoxybenzyl)oxy)-4-((trimethylsilyl)ethynyl)pyridin-2-yl)methyl acetate (5.38 g, 11.1 mmol) which is a crude product obtained in a-5) was dissolved in dichloromethane (55 mL), added trimethylsilane (1.9 mL, 35.1 mmol) and trifluoroacetate (5.5 mL) at room temperature, and the mixture was stirred overnight. The reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions (pH=8 was confirmed). The reaction solution was filtered through a pad of celite. The obtained filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (1.54 g (yield 53%)) was obtained as a yellow oil.

Workup

  1. customobtained in a-5)
  2. filtrationThe reaction solution was filtered through a pad of celite
  3. extractionThe obtained filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e0fc05b143dc4d9b9ee0970151055544
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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