Methyl 9-bromononanoate → HCID 15725722, compound

HRID 982072Notes

Reaction equation

HRID 982072 reaction equation
C1([C:7]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]=[N:8]2)C=CC=CC=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34]>CN(C)C=O.CCCCCC.C(OCC)C>[C:18]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[N:8]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 554142Methyl 9-bromononanoateHCID 19982286HCID 19982286, compound

Product 1

HCID 15725722HCID 15725722, compoundYield 202.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

Sodium hydride (588 mg of a 60% dispersion in mineral oil, 13 mmol) was washed twice with hexane and covered with dimethylformamide (DMF), (45 mL). 3,3,5-Triphenyl-3H-pyrazole (3 g, 10 mmol) was added and the mixture stirred at 110° C. under a nitrogen atmosphere for 30 minutes before being cooled to room temperature. Methyl 9-bromononanoate (2.80 g, 11 mmol) in DMF (2 mL) was added dropwise, the mixture stirred at room temperature for 2 hours and then poured onto water (100 mL). The mixture was extracted with diethyl ether (3×100 mL), the extracts washed with water (3×100 mL), dried over sodium sulfate and concentrated to give an oil. Chromatography on a column of silica gel using a mixture of hexane and diethyl ether (2:1) as eluent afforded methyl 3,4,5-triphenyl-lH-pyrazol-1-nonanoate (4.72 g, 100%) as a viscous oil. (MS(CI): m/e =467 (MH+).

Workup

  1. washSodium hydride (588 mg of a 60% dispersion in mineral oil, 13 mmol) was washed twice with hexane
  2. temperaturebefore being cooled to room temperature
  3. stirringthe mixture stirred at room temperature for 2 hours
  4. additionpoured onto water (100 mL)
  5. extractionThe mixture was extracted with diethyl ether (3×100 mL)
  6. washthe extracts washed with water (3×100 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give an oil

Sources & evidence

ORD record
ord-156272ed273a4a6287c57ddb30c7521c
Source dataset
uspto-grants-1991_02
Patent number
US04994482

Reaction notes

Loading…