Water → HCID 15725737, compound

HRID 982066Notes

Reaction equation

HRID 982066 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][C:32]([O:34][CH2:35][CH3:36])=[O:33].O>CCCCCC.CN(C)C=O.C(OCC)C>[C:3]1([C:9]2[C:13]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[N:10]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 19982286HCID 19982286, compound

Product 1

HCID 15725737HCID 15725737, compoundYield 199.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent2×

Conditions

Temperature
110 °C

Procedure

Sodium hydride (1.30 g of 60% dispersion, 32 mmol) was washed twice with hexane and covered with dimethylformamide (DMF) (100 mL). 3,3,5-Triphenyl-3H-pyrazole (8 g, 27 mmol) was added and the mixture stirred at 110° C. under an atmosphere of nitrogen for 25 minutes before being cooled to room temperature. Ethyl 6-bromohexanoate (6.6 g, 5.3 mL, 29 mmol) in DMF (2 mL) was added dropwise and the mixture stirred at room temperature. After 15 minutes water was added and the mixture extracted with diethyl ether (4 times). The combined extracts were washed with water (3 times), dried and concentrated in vacuo to give an oil. Chromatography on a column of silica gel using a mixture of hexane and diethyl ether (11:9) as eluent afforded ethyl 3,4,5-triphenyl-lH-pyrazol-1-hexanoate (11.83 g, 100%) as a viscous oil. MS(CI): m/e =439 (MH+).

Workup

  1. temperaturebefore being cooled to room temperature
  2. stirringthe mixture stirred at room temperature
  3. extractionthe mixture extracted with diethyl ether (4 times)
  4. washThe combined extracts were washed with water (3 times)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto give an oil

Sources & evidence

ORD record
ord-ffdd393db6674d6ab849ebb72cf2cd7a
Source dataset
uspto-grants-1991_02
Patent number
US04994482

Reaction notes

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