Sodium hydride → HCID 67794438, compound

HRID 1460709Notes

Reaction equation

HRID 1460709 reaction equation
[H-].[Na+].[C:3]1([C:9]2(C3C=CC=CC=3)[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[N:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH2:37]>CN(C=O)C>[C:3]1([C:9]2[C:13]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][N:10]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:27]=[CH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28414811-Bromo-1-undeceneHCID 19982286HCID 19982286, compound

Product 1

HCID 67794438HCID 67794438, compoundYield 181.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of sodium hydride (50% dispersion, 0.2 g, 4 mmol, prewashed with hexane) and 3,3,5-triphenyl-3H-pyrazole (1.00 g, 3.4 mmol) in DMF (15mL) was heated to 110° C. under an atmosphere of nitrogen. After 50 minutes, the solution was cooled to room temperature and 11-bromoundecene (0.81 g, 3.7 mmol) added. The mixture was stirred at room temperature overnight, poured onto water and extracted with diethyl ether. The combined extracts were washed with water (3×), and saturated sodium chloride solution, dried and the solvent removed. The residue was chromatographed on a column of silica gel using a mixture of hexane and ethyl acetate (9:1) containing 1% triethyl amine to give 3,4,5-triphenyl-1H-pyrazole -1-undecene (1.51 g, 100%) as an oil. MS(CI): m/e=448 (MH+).

Workup

  1. temperaturethe solution was cooled to room temperature
  2. additionpoured onto water
  3. extractionextracted with diethyl ether
  4. washThe combined extracts were washed with water (3×), and saturated sodium chloride solution
  5. customdried
  6. customthe solvent removed
  7. customThe residue was chromatographed on a column of silica gel using
  8. additiona mixture of hexane and ethyl acetate (9:1)
  9. additioncontaining 1% triethyl amine

Sources & evidence

ORD record
ord-3036a0922e3e4c37855a431118540994
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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