Water → HCID 22335334, compound

HRID 586719Notes

Reaction equation

HRID 586719 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].F[C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([F:19])[C:10]=1[C:11]#[N:12].O>O1CCCC1>[F:19][C:13]1[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:9]([O:7][CH2:6][CH2:5][O:4][CH3:3])[C:10]=1[C:11]#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 27787722,6-Difluoro-4-methoxybenzonitrile

Product 1

HCID 22335334HCID 22335334, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in mineral oil, 0.88 g, 22 mmol) was added to 2-methoxyethanol (1.84 g, 24 mmol) in tetrahydrofuran (20 ml) and the mixture was stirred at room temperature for 20 minutes. 2,6-Difluoro-4-methoxy-benzonitrile (Mol. Cryst. Liq. Cryst. 1989, 172) (3.38 g, 20 mmol) was added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and the solution was extracted with dichloromethane (3×50 ml). The combined organic solutions were dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using methanol in dichloromethane as eluant (gradient from 0:100 to 3:97) to give the title compound (3.8 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionthe solution was extracted with dichloromethane (3×50 ml)
  3. dry with materialThe combined organic solutions were dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6dbe55e922144499bb94d8ec2b197020
Source dataset
uspto-grants-2005_08
Patent number
US06936619B2

Reaction notes

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