Aluminium lithium hydride → HCID 21389866, compound

HRID 1833706Notes

Reaction equation

HRID 1833706 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([CH3:20])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([CH3:19])[C:10]=2[CH2:9][CH2:8][O:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O1CCCC1>O1CCCC1>[CH3:20][C:6]1([CH2:5][CH2:4][OH:3])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([CH3:19])[C:10]=2[CH2:9][CH2:8][O:7]1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 53998609HCID 53998609, compound

Product 1

HCID 21389866HCID 21389866, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,5-dimethyl-1,3,4,5-tetrahydropyrano[4,3-b]indole-1-acetic acid ethyl ester (17.0 g), described in Example 916, in tetrahydrofuran (200 ml) is added dropwise to a suspension of lithium aluminium hydride (5.0 g) in tetrahydrofuran (150 ml). The mixture is heated at reflux for 2.5 hr. and then cooled and treated with a mixture of water-tetrahydrofuran (30 ml - 150 ml). The mixture is filtered through celite and the filtrate is evaporated. The residue is purified by chromatography on silica gel. Elution with chloroform gives 1,5-dimethyl-1,3,4,5-tetrahydropyrano[4,3-b]indole-1-ethanol.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2.5 hr
  3. temperatureand then cooled
  4. filtrationThe mixture is filtered through celite
  5. customthe filtrate is evaporated
  6. customThe residue is purified by chromatography on silica gel
  7. washElution with chloroform

Sources & evidence

ORD record
ord-4a1c3d4552874a0f82597bf9a8da0c1a
Source dataset
uspto-grants-1978_01
Patent number
US04066780

Reaction notes

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