Hydrochloric Acid → HCID 20092143, compound

HRID 274186Notes

Reaction equation

HRID 274186 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[CH:25]([O:27][CH2:28][CH3:29])[CH3:26].[OH-].[Na+].Cl>O.C(O)C>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:26][CH2:25][O:27][CH2:28][CH3:29])=[C:18]([F:23])[N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 145479151-Bromo-1-ethoxyethaneHCID 190469612-(4-Octyloxyphenyl)-5-hydroxy-6-fluoropyridine

Product 1

HCID 20092143HCID 20092143, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.1 mol of 2C, 0.1 mol of 1-bromoethoxyethane, 0.1 mol of sodium hydroxide, 20 ml of ethanol and 50 ml of water is heated at the boil for 2 hours. The mixture is cooled, dilute hydrochloric acid is added, and the aqueous phase is extracted with dichloromethane. The solvent is removed under reduced pressure, and the residue is purified by column chromatography, giving the product 2-(4-octyloxyphenyl)-5-(2-ethoxyethoxy)-6-fluoropyridine.

Workup

  1. temperatureis heated at the boil for 2 hours
  2. temperatureThe mixture is cooled
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-4e0bc83878c14500884c11b6594ab2ff
Source dataset
uspto-grants-1995_02
Patent number
US05389291

Reaction notes

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