Sodium sulfate decahydrate → Indolizin-7-ol

HRID 1796204Notes

Reaction equation

HRID 1796204 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1[C:15]2[N:10]([CH:11]=[CH:12][C:13](=[O:16])[CH:14]=2)[CH2:9][CH:8]=1.C(OC(OCC)CCCN)C.CCOC(CC(CC(OCC)=O)=O)=O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH:7]1[CH:8]=[CH:9][N:10]2[C:15]=1[CH:14]=[C:13]([OH:16])[CH:12]=[CH:11]2

Participants

7

Reactant 5

HCID 62649Sodium sulfate decahydrateHCID 66045Diethyl acetonedicarboxylateHCID 806724,4-DiethoxybutylamineHCID 21226445Aluminium lithium hydrideHCID 69592000HCID 69592000, compound

Product 1

HCID 22180983Indolizin-7-olYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (2.30 g) in tetrahydrofuran (50 ml) was added dropwise indolizin-7-one (2.80 g), which was prepared from 4,4-diethoxybutylamine and diethyl 1,3-acetonedicarboxylate according to the method described in Heterocycles, 43, 1391 (1996), with stirring under ice-cooling under a nitrogen atmosphere, and the resulting mixture was stirred at the same temperature for 1 hour. After stirring, to the reaction mixture was added sodium sulfate decahydrate, and the resulting mixture was furthermore stirred at room temperature for 1 hour. After removing insoluble materials by filtration, the filtrate was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and methanol (4:1) as the eluent to afford the title compound (1.70 g, yield: 59%) as a yellow oil.

Workup

  1. temperaturecooling under a nitrogen atmosphere
  2. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  3. stirringAfter stirring, to the reaction mixture
  4. stirringthe resulting mixture was furthermore stirred at room temperature for 1 hour
  5. customAfter removing insoluble materials
  6. filtrationby filtration
  7. customthe filtrate was evaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-9a2aeef1ee1b4da0bb01d0592c1642a7
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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