Chlorotriethylsilane → 4-[2,2,2-Trifluoro-1-(triethylsilyloxy)ethyl]pyridine

HRID 1880760Notes

Reaction equation

HRID 1880760 reaction equation
[F:1][C:2]([F:12])([F:11])[CH:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[OH:4].[CH2:13]([Si:15](Cl)([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14].[Cl-].[NH4+]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[F:12][C:2]([F:1])([F:11])[CH:3]([C:5]1[CH:6]=[CH:7][N:8]=[CH:9][CH:10]=1)[O:4][Si:15]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 13819ChlorotriethylsilaneHCID 25517Ammonium ChlorideHCID 595703722,2,2-trifluoro-1-(pyridin-4-yl)ethan-1-ol

Product 1

HCID 595702944-[2,2,2-Trifluoro-1-(triethylsilyloxy)ethyl]pyridineYield 98.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 20 ml of pyridine were added 3.4 g of 2,2,2-trifluoro-1-pyridin-4-yl-ethanol and 1.17 g of 4-dimethylaminopyridine, and 3.76 g of triethylsilyl chloride was added at 0° C. After stirring at room temperature for 4 hours, the mixture was poured into an aqueous saturated ammonium chloride solution, followed by extraction with t-butyl methyl ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 5.5 g of 4-[2,2,2-trifluoro-1-(triethylsilyloxy)ethyl]pyridine.

Workup

  1. additionwas added at 0° C
  2. extractionfollowed by extraction with t-butyl methyl ether three times
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4363c002353b4f9f8665825f364b18c2
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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