Water → HCID 131716802, compound

HRID 982068Notes

Reaction equation

HRID 982068 reaction equation
[C:1]1([C:7]2(C3C=CC=CC=3)[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].O>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[OH2:33].[C:1]1([C:7]2[C:11]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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][C:32]([O:34][CH2:35][CH3:36])=[O:33])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH2:35]([O:34][C:32](=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:9]1[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8]1)[CH3:36]

Participants

7

Reactant 3

HCID 962WaterHCID 264813Ethyl 8-bromooctanoateHCID 19982286HCID 19982286, compound

Product 1

HCID 131716802HCID 131716802, compoundYield 127.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
110 °C

Procedure

Sodium hydride (0.58 g of a 50% dispersion, 12 mmol) was washed twice with hexane and covered with DMF (45 mL). 3,3,5-Triphenyl-3H-pyrazole (3 g, 10 mmol) was added and the mixture heated at 110° C. under nitrogen for 45 minutes before being cooled to room temperature. A solution of ethyl 8-bromo-octanoate (2.80 g, 11 mmol) in DMF (2 mL) was added and the mixture stirred for 10 minutes before being poured onto a mixture of water and ethyl acetate. The aqueous layer was discarded and the organic layer washed twice with water and once with saturated sodium chloride solution. The organic phase was dried over sodium sulfate and concentrated to afford an oil. Chromatography on a column of silica gel using a mixture of hexane and ethyl acetate (17:3) as eluent gave ethyl 3,4,5-triphenyl-lH-pyrazol-1-octanoate hemihydrate (4.05 g, 85%) as an oil. MS(CI): m/e =467 (MH+).

Workup

  1. washSodium hydride (0.58 g of a 50% dispersion, 12 mmol) was washed twice with hexane
  2. temperaturebefore being cooled to room temperature
  3. washthe organic layer washed twice with water and once with saturated sodium chloride solution
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford an oil

Sources & evidence

ORD record
ord-37e18c5dcdd145138143831229b967ac
Source dataset
uspto-grants-1991_02
Patent number
US04994482

Reaction notes

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