1-Iodohexane → HCID 20095029, compound

HRID 1770157Notes

Reaction equation

HRID 1770157 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]3[N:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=4)=[CH:20][N:19]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[K+].[CH2:33](I)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C(O)CCC>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]3[N:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:26][CH:25]=4)=[CH:20][N:19]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 125271-IodohexaneHCID 14797Potassium HydroxideHCID 20095042HCID 20095042, compound

Product 1

HCID 20095029HCID 20095029, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

0.25 g (0.62 mM) of 2-octyl-5-[5-(4-hydroxyphenyl)pyrimidine-2-yl]indan, 0.07 g of 85% -potassium hydroxide, 0.2 ml of hexyl iodide and 5 ml of n-butanol were placed in a 20 ml-round bottomed flask, followed by heat-refluxing for 3.5 hours under stirring. After the reaction, the reaction mixture was poured into ice water. The resultant insoluble matter was recovered by filtration and dissolved in toluene, followed by washing with 3%-sodium thiosulfate aqueous solution. The water layer was subjected to extraction with toluene and the resultant toluene layer was added to the organic layer, followed by washing with saturated common salt aqueous solution, drying with anhydrous sodium sulfate and distilling-off of the solvent. The resultant crude product was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.23 g of 2-octyl-5-[5-(4-hexyloxyphenyl)pyrimidine-2-yl]indan (Yield: 76.0%). ##STR139##

Workup

  1. temperatureby heat-refluxing for 3.5 hours
  2. customAfter the reaction
  3. filtrationThe resultant insoluble matter was recovered by filtration
  4. dissolutiondissolved in toluene
  5. washby washing with 3%-sodium thiosulfate aqueous solution
  6. extractionThe water layer was subjected to extraction with toluene
  7. additionthe resultant toluene layer was added to the organic layer
  8. washby washing with saturated common salt aqueous solution
  9. dry with materialdrying with anhydrous sodium sulfate and distilling-off of the solvent
  10. customThe resultant crude product was purified by silica gel column chromatography (eluent: toluene)
  11. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-723122083b2c41f89fd41efcd67d90b4
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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