Sodium hydride → HCID 67794438, compound

HRID 982078Notes

Reaction equation

HRID 982078 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 (15 mL) 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 x), 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-lH-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 x), 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-d328efdb79c247f387ed312673e9e94b
Source dataset
uspto-grants-1991_02
Patent number
US04994482

Reaction notes

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