Tetrahydrofuran → HCID 20400799, compound

HRID 1980862Notes

Reaction equation

HRID 1980862 reaction equation
C(OC([CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:29]1CCCC1>>[OH:29][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 20400783HCID 20400783, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20400799HCID 20400799, compound

Procedure

To 10.0 g of 3-(2-ethoxycarbonylethyl)-2-(3-pyridyl)indole in 400 ml of dry tetrahydrofuran at 0° is added 60 ml of a 1M solution of lithium aluminum hydride in tetrahydrofuran. This is allowed to stir at room temperature for 1 hour, then cooled by an ice bath and quenched successively with 2.26 ml of water, 2.26 ml of a 15% sodium hydroxide solution, and 6.78 ml of water. The mixture is filtered, concentrated in vacuo, and the residue dissolved in ether, washed with a saturated NaHCO3 solution, dried over MgSO4 and concentrated in vacuo to give 3-(2-hydroxyethyl)-2-(3-pyridyl)-indole.

Workup

  1. temperaturecooled by an ice bath
  2. customquenched successively with 2.26 ml of water, 2.26 ml of a 15% sodium hydroxide solution, and 6.78 ml of water
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated in vacuo
  5. dissolutionthe residue dissolved in ether
  6. washwashed with a saturated NaHCO3 solution
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c76bcfd6e62441a82e97bf49823334d
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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