Sodium hydride → 4-[2-[4-(1,1-Dimethylethyl)phenyl]ethoxy]-8-fluoroquinoline

HRID 1196476Notes

Reaction equation

HRID 1196476 reaction equation
[H-].[Na+].[CH3:3][C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].Cl[C:17]1[C:26]2[C:21](=[C:22]([F:27])[CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][CH:18]=1>CN(C=O)C>[C:4]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][O:15][C:17]2[C:26]3[C:21](=[C:22]([F:27])[CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)=[CH:11][CH:12]=1)([CH3:3])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79410p-tert-Butylphenethyl alcoholHCID 27365874-Chloro-8-fluoroquinoline

Product 1

HCID 1641904-[2-[4-(1,1-Dimethylethyl)phenyl]ethoxy]-8-fluoroquinolineYield 32.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 1.1 g of sodium hydride in 50 mL of DMF was added 4.0 g of 2-[4-(1,1-dimethylethyl)phenyl]ethyl alcohol, and the mixture was stirred for one hour at room temperature. Then 4.0 g of 4-chloro-8fluoroquinoline in 20 mL of DMF were added, and the mixture was stirred at room temperature overnight. Then the mixture was poured into an ice/water mixture, and the solid was collected and recrystallized from ethyl acetate/pentane to give 2.3 g of the title product. Yield 32.4%. M.P. 81°-82° C.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customthe solid was collected
  3. customrecrystallized from ethyl acetate/pentane

Sources & evidence

ORD record
ord-805748d9f65a471caaa7f69813c8933f
Source dataset
uspto-grants-1992_05
Patent number
US05114939

Reaction notes

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