Water → HCID 14769997, compound

HRID 477050Notes

Reaction equation

HRID 477050 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].Br[C:10]1[CH:22]=[CH:21][C:13]([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=1.O>CN(C=O)C.[Cu](I)I>[F:1][C:2]([F:6])([F:5])[CH2:3][O:4][C:10]1[CH:22]=[CH:21][C:13]([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 19837307HCID 19837307, compound

Product 1

HCID 14769997HCID 14769997, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a stream of nitrogen, 2.0 ml of 2,2,2-trifluoroethanol was added to 52.8 mg of sodium hydride, and then a solution of 140 mg of copper iodide and 922 mg of 4-(4-bromobenzyl)pyridine in 4 ml of N,N'-dimethylformamide was added. The mixture was stirred at a bath temperature of 120° C. for 3 hours. After the reaction, water was added to the reaction mixture, and it was extracted with ethyl acetate. The extract was washed with water, and the solvent was evaporated. 0.78 g of the residue was distilled under reduced pressure by using a Kugel-Rohr. When 574 mg (yield 57%) of a fraction having a boiling point of 150° C. (0.2 mmHg) was separated, 4-[4-(2,2,2-trifluoroethoxy)benzyl]pyridine was obtained as colorless crystals having a melting point of 51° to 53° C.

Workup

  1. additionwas added to the reaction mixture, and it
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customthe solvent was evaporated
  5. distillation0.78 g of the residue was distilled under reduced pressure
  6. customwas separated

Sources & evidence

ORD record
ord-039eee98b8224f49b3c3ceac1c0b23d6
Source dataset
uspto-grants-1989_12
Patent number
US04886822

Reaction notes

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