Toluene → HCID 15725739, compound

HRID 1460696Notes

Reaction equation

HRID 1460696 reaction equation
[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].[OH-].[Na+].C1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 15725738HCID 15725738, compound

Product 1

HCID 15725739HCID 15725739, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 3,4,5-triphenyl-1H-pyrazol-1-hexanol (5 g, 12 mmol), tert-butyl bromoacetate (4.92 g, 4.10 mL, 25 mmol), tetrabutylammonium hydrogen sulfate (0.4 g), 50% aqueous sodium hydroxide solution (80 mL) and toluene (80 mL) was stirred vigorously at room temperature. After I8 hours, the reaction mixture was diluted with water (100 mL), the organic layer separated and the aqueous layer extracted twice with diethyl ether. The combined extracts were dried over sodium sulfate and the solvent evaporated to give an oil which was chromatographed on a column of silica gel. Elution with a mixture of hexane and diethyl ether (2:1) afforded 1,1-dimethylethyl [[6-(3,4,5-triphenyl-1H-pyrazol-1-yl)hexyl]oxy]-acetate (5.84 g, 95%) as an oil that slowly crystallized to a white solid; m.p.=69°-72° C. MS(CI): m/e=511 (MH+).

Workup

  1. waitAfter I8 hours
  2. customthe organic layer separated
  3. extractionthe aqueous layer extracted twice with diethyl ether
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customthe solvent evaporated
  6. customto give an oil which
  7. customwas chromatographed on a column of silica gel
  8. washElution
  9. additionwith a mixture of hexane and diethyl ether (2:1)

Sources & evidence

ORD record
ord-1c95efb870474cfcad9b8eccb12efe35
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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