Aluminium lithium hydride → HCID 68535380, compound

HRID 2389344Notes

Reaction equation

HRID 2389344 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[OH:2][CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21716281tert-Butyl 3-(3-methoxy-3-oxopropyl)-1H-indole-1-carboxylate

Product 1

HCID 68535380HCID 68535380, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring solution of tert-butyl 3-(3-methoxy-3-oxopropyl)-1H-indole-1-carboxylate (50 mg) was added lithium aluminum hydride (6 mg) at 0° C. After 1 hour, to the mixture was added water, and the resulting mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=5:1) to give tert-butyl 3-(3-hydroxypropyl)-1H-indole-1-carboxylate (45 mg).

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=5:1)

Sources & evidence

ORD record
ord-fbb49656475047ea9ad61e44f2a7ba6e
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…