Hydrochloric Acid → HCID 18441928, compound

HRID 458441Notes

Reaction equation

HRID 458441 reaction equation
[H-].[Na+].[C:3](#[N:5])[CH3:4].[F:6][C:7]([F:22])([F:21])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](OCC)=[O:17])=[CH:10][CH:9]=1.Cl>C1COCC1.O>[O:17]=[C:16]([CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([F:6])([F:21])[F:22])=[CH:9][CH:10]=1)[CH2:4][C:3]#[N:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 11858695Ethyl 3-[4-(trifluoromethyl)phenyl]propanoate

Product 1

HCID 18441928HCID 18441928, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (40 mmol) in THF (50 ml) was added acetonitrile (5.2 ml, 100 mmol) dropwise. The the resulting anion was added a solution of ethyl 3-[4-(trifluoromethyl)phenyl]propanoate (34.4 mmol) in THF (10 ml). The reaction mixture was refluxed for 3 h and then allowed to cool. To the resulting slurry was added water (50 ml) and the solution was acidified to pH 2 with 6 N HCl. The aqueous solution was extracted three times with diethyl ether. The organic layer was dried (Na2SO4) and concentrated. The product was purified by silica gel column chromatography (silica gel/25% ethyl acetate in petroleum ether) giving A as an oil (4.36 g, 53% yield). 1H NMR (300 MHz, CDCl3) δ 7.47 (m, 2H), 7.31 (m, 2H), 3.44 (s, 2H), 2.99 (s, 4H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. temperatureto cool
  3. extractionThe aqueous solution was extracted three times with diethyl ether
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe product was purified by silica gel column chromatography (silica gel/25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-41d62bb71254474aa6b5c6a3d12d3f4f
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

Loading…