2H-Pyran, 2-[(8-bromooctyl)oxy]tetrahydro- → 3-(8-Hydroxyoctyl)-2-(3-pyridyl)-indole

HRID 1980858Notes

Reaction equation

HRID 1980858 reaction equation
C([Mg]Br)C.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=1.O1CCCCC1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]Br>O1CCCC1>[OH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:7]1[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1709162H-Pyran, 2-[(8-bromooctyl)oxy]tetrahydro-HCID 6066772-(pyridin-3-yl)-1H-indoleHCID 178418443HCID 178418443, compound

Product 1

HCID 204007953-(8-Hydroxyoctyl)-2-(3-pyridyl)-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 30 ml of a 2M solution of ethylmagnesium bromide in tetrahydrofuran under nitrogen at 0°-5° is added dropwise over 30 minutes a solution of 10.0 g of 2-(3-pyridyl)indole in 60 ml of tetrahydrofuran. The mixture is stirred for 0.5 hour at 0°-5° followed by the dropwise addition of 17.6 g of 1-tetrahydropyranyloxy-8-bromooctane in 50 ml of tetrahydrofuran. After stirring at 0°-10° for 1 hour and at room temperature for 0.5 hour, the reaction mixture is poured into ice-water and extracted with ether. The ether extract is washed with water, dried over MgSO4 and evaporated to dryness. The residue is dissolved in 100 ml of 3N hydrochloric acid, the resulting mixture is kept at room temperature for 0.5 hour, washed with ether, basified with aqueous with 3N sodium hydroxide solution and extracted with methylene chloride. The methylene chloride solution is evaporated to dryness to give 3-(8-hydroxyoctyl)-2-(3-pyridyl)-indole.

Workup

  1. stirringAfter stirring at 0°-10° for 1 hour and at room temperature for 0.5 hour
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. dissolutionThe residue is dissolved in 100 ml of 3N hydrochloric acid
  8. waitthe resulting mixture is kept at room temperature for 0.5 hour
  9. washwashed with ether
  10. extractionextracted with methylene chloride
  11. customThe methylene chloride solution is evaporated to dryness

Sources & evidence

ORD record
ord-056c6a07519a436984a5a7fbe9371818
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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