1-Bromononane → 2-(5-Chloro-2-(n-nonyloxy)phenyl)-1-(1h-1-imidazolyl)-2-propanol

HRID 1582621Notes

Reaction equation

HRID 1582621 reaction equation
[OH-].[Na+].[CH2:3](Br)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:21]([OH:29])([CH3:28])[CH2:22][N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)[CH:15]=1>CN(C)C=O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[C:16]([C:21]([OH:29])([CH3:28])[CH2:22][N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)[CH:15]=1

Participants

5

Reactant 3

HCID 127421-BromononaneHCID 14798Sodium HydroxideHCID 129728974-chloro-2-(1-hydroxy-2-(1H-1-imidazolyl)-1-methylethyl)phenol2×

Product 1

HCID 99078142-(5-Chloro-2-(n-nonyloxy)phenyl)-1-(1h-1-imidazolyl)-2-propanolYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydroxide powder (20 mg, 0.5 mmol) and n-nonyl bromide (122 mg, 0.59 mmol) were added to a solution of 4-chloro-2-(1-hydroxy-2-(1H-1-imidazolyl)-1-methylethyl)phenol [compound (2-1)] (100 mg, 0.40 mmol) in N,N-dimethylformamide (1 mL), and the mixture was stirred for 17 hours at room temperature. Ice-water was added to the resultant mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography and dried under reduced pressure, to thereby yield 2-(5-chloro-2-(n-nonyloxy)phenyl)-1-(1H-1-imidazolyl)-2-propanol as a colorless oily product (81.7 mg, yield: 54.5%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified through silica gel column chromatography
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-859e93c5465c470a8b29dca6b46c05bf
Source dataset
uspto-grants-2004_05
Patent number
US06737434B2

Reaction notes

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