Iodoethane → 1-(4-bromo-2,6-dimethylphenyl)4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-1H-pyrazole

HRID 1740109Notes

Reaction equation

HRID 1740109 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([N:11]2[C:15]([CH2:16][CH3:17])=[C:14]([CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][C:20]=3[OH:29])[C:13]([CH2:30][CH3:31])=[N:12]2)=[C:6]([CH3:32])[CH:5]=1.I[CH2:34][CH3:35]>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]([CH3:32])[C:7]([N:11]2[C:15]([CH2:16][CH3:17])=[C:14]([CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][C:20]=3[O:29][CH2:34][CH3:35])[C:13]([CH2:30][CH3:31])=[N:12]2)=[C:8]([CH3:10])[CH:9]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 537145601-[1-(4-Bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-naphthalene-2-ol

Product 1

HCID 218373011-(4-bromo-2,6-dimethylphenyl)4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-1H-pyrazoleYield 26.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% mineral oil dispersion, 0.337 g, 8.4 mmol) was added portionwise to a solution of 1-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-naphthalene-2-ol (1.30 g, 8.4 mmol) in 12 ml anhydrous tetrahydrofuran. After stirring 5 minutes, iodoethane (1.12 ml, 14 mmol) was added, and the resulting reaction mixture was stirred 16 hours at ambient temperature. The solvent was removed in vacuo, and the residue was then extracted with methylene chloride/water (25 ml of each). The aqueous phase was twice extracted with 25 ml portions of fresh methylene chloride. The combined organic extracts were dried (anhydrous sodium sulfate), and concentrated in vacuo to an oily solid (1.92 g). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes =6:94 in volume) afforded 1.1 g of the title compound as an off white solid.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred 16 hours at ambient temperature
  3. customThe solvent was removed in vacuo
  4. extractionthe residue was then extracted with methylene chloride/water (25 ml of each)
  5. extractionThe aqueous phase was twice extracted with 25 ml portions of fresh methylene chloride
  6. dry with materialThe combined organic extracts were dried (anhydrous sodium sulfate)
  7. concentrationconcentrated in vacuo to an oily solid (1.92 g)
  8. washFlash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes =6:94 in volume)

Sources & evidence

ORD record
ord-f1b9124a4e1b406fb90a8bee3ae149b2
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

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