Diethylene Glycol → HCID 20095032, compound

HRID 1770173Notes

Reaction equation

HRID 1770173 reaction equation
[CH2:1]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22](=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:18][N:17]=3)[CH:13]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O)COCCO.O.NN.[OH-].[K+]>C(OCC)(=O)C.O>[CH2:1]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:18][N:17]=3)[CH:13]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20095006HCID 20095006, compound

Product 1

HCID 20095032HCID 20095032, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.50 g (1.15 mM) of 2-hexyl-5-(5-decanoylpyridine-2-yl) indan, 3.5 ml of diethylene glycol, 0.18 ml (2.96 mM) of 80%-hydrazine hydrate (density: 1.03), and 0.23 g (3.48 mM) of 85%-KOH were mixed and heat-stirred for 1 hour at 144°-216° C. After the reaction, the reaction mixture was poured into water, followed by addition of ethyl acetate and saturated common salt aqueous solution and stirring at room temperature to obtain an insoluble matter through filtration under reduced pressure. The insoluble matter was dissolved in toluene and dried with anhydrous sodium sulfate. The filtrate was subjected to extraction with ethyl acetate and washed with saturated common salt aqueous solution, followed by drying with anhydrous sodium sulfate. Each of the sodium sulfate was removed by filtration and each of the filtrate (toluene solution and ethyl acetate solution) was evaporated into a residue. The thus-prepared two-species of residues were mixed and purified by silica gel column chromatography (eluent: toluene), followed by concentration. To the concentrated matter, methanol was added, followed by cooling in a refrigerator. After the cooling, the resultant insoluble matter was recovered by filtration to obtain 0.18 g of 2-hexyl-5-(5-decylpyridine-2-yl)indan (Yield: 37.2%). ##STR306##

Workup

  1. customAfter the reaction
  2. stirringstirring at room temperature
  3. customto obtain an insoluble matter
  4. filtrationthrough filtration under reduced pressure
  5. dissolutionThe insoluble matter was dissolved in toluene
  6. dry with materialdried with anhydrous sodium sulfate
  7. extractionThe filtrate was subjected to extraction with ethyl acetate
  8. washwashed with saturated common salt aqueous solution
  9. dry with materialby drying with anhydrous sodium sulfate
  10. customEach of the sodium sulfate was removed by filtration
  11. customeach of the filtrate (toluene solution and ethyl acetate solution) was evaporated into a residue
  12. customThe thus-prepared two-species of residues
  13. additionwere mixed
  14. custompurified by silica gel column chromatography (eluent: toluene)
  15. concentrationfollowed by concentration
  16. additionTo the concentrated matter, methanol was added
  17. temperatureby cooling in a refrigerator
  18. filtrationAfter the cooling, the resultant insoluble matter was recovered by filtration

Sources & evidence

ORD record
ord-736e7ab00ebb41c6b72744456fa34bcb
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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