HCID 13362108, compound → HCID 20441682, compound

HRID 1633136Notes

Reaction equation

HRID 1633136 reaction equation
CC[O:3][C:4]([CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[C:8]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:3][CH2:4][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[C:8]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 13362108HCID 13362108, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20441682HCID 20441682, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 11.77 g of 1-(2-ethoxycarbonylmethyl)-2-(3-pyridyl)-3-methylindole in 400 ml of dry tetrahydrofuran at 0° is added 60 ml of a 1 M 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. There is obtained the semi-solid 1-(2-hydroxyethyl)-2-(3-pyridyl)-3-methylindole which is used directly in the next step.

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-17c45796a931443daa6d53833095ef50
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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