Iodoethane → 4-(2-Ethoxy-naphthalen-1-ylmethyl)-1-[4(1-ethoxy-propyl)-2,6-dimethylphenyl]-3,5-diethyl-1H-pyrazole

HRID 1740114Notes

Reaction equation

HRID 1740114 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:16][C:17]1[C:18]([CH2:36][CH3:37])=[N:19][N:20]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([CH:31]([OH:34])[CH2:32][CH3:33])=[CH:26][C:25]=2[CH3:35])[C:21]=1[CH2:22][CH3:23])[CH3:4].I[CH2:39][CH3:40].C(Cl)Cl>O1CCCC1>[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:16][C:17]1[C:18]([CH2:36][CH3:37])=[N:19][N:20]([C:24]2[C:25]([CH3:35])=[CH:26][C:27]([CH:31]([O:34][CH2:39][CH3:40])[CH2:32][CH3:33])=[CH:28][C:29]=2[CH3:30])[C:21]=1[CH2:22][CH3:23])[CH3:4]

Participants

6

Reactant 4

HCID 6340Iodoethane2×HCID 6344DichloromethaneHCID 24758Sodium hydride3×HCID 218373291-{4-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-propan-1-ol

Product 1

HCID 218373424-(2-Ethoxy-naphthalen-1-ylmethyl)-1-[4(1-ethoxy-propyl)-2,6-dimethylphenyl]-3,5-diethyl-1H-pyrazoleYield 146.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% mineral oil dispersion, 0.031 g, 0.78 mmol) was added portionwise to a solution of 1-{4-[4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-propan-1-ol (0.123 g, 0.26 mmol) in 0.5 ml anhydrous tetrahydrofuran. After stirring 5 minutes, iodoethane (0.104 ml, 1.3 mmol) was added and the resulting mixture was stirred for 16 hours at ambient temperature. A second portion of sodium hydride (0.031 g of a 60% sodium hydride mineral oil dispersion; 0.78 mmol) was added, followed by a second portion of iodoethane (0.104 ml, 1.3 mmol). After stirring at ambient temperature for 4 hours, the reaction mixture was well-mixed with methylene chloride/aqueous sodium bicarbonate (10 ml of each). The aqueous phase was then twice extracted with 10 ml portions of fresh methylene chloride. The combined organic extracts were then dried over anhydrous sodium sulfate and concentrated in vacuo to afford a 190 mg residue. Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes=1:4 in volume) afforded the title compound (45 mg) as an oil.

Workup

  1. stirringthe resulting mixture was stirred for 16 hours at ambient temperature
  2. addition0.78 mmol) was added
  3. stirringAfter stirring at ambient temperature for 4 hours
  4. extractionThe aqueous phase was then twice extracted with 10 ml portions of fresh methylene chloride
  5. dry with materialThe combined organic extracts were then dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd4bc209f2424709a4f985b907ea62f1
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

Loading…