Aluminium lithium hydride → 10H-Phenoxazine-10-ethanol

HRID 2219779Notes

Reaction equation

HRID 2219779 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:18]1[C:19]2[N:6]([CH2:5][CH2:4][OH:3])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:13][C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53780817Ethyl-2-(10H-phenoxazin-10-yl)acetate

Product 1

HCID 1017692410H-Phenoxazine-10-ethanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl-2-(10H-phenoxazin-10-yl)acetate (5.5 g, 20.44 mmol) in dry tetrahydrofuran (20 ml) was added dropwise to a suspension of lithium aluminum hydride (1.16 g, 30.52 mmol) in dry tetrahydrofurane (20 ml) at 0° C. The reaction mixture was warmed to room temperature and stirred for additional 1 h. The excess lithium aluminum hydride was quenched with a solution of saturated sodium sulfate at 0° C. The reaction mixture was filtered and the residue was washed with hot ethyl acetate (2×75 ml). The combined organic layers were dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure to afford the title compound (4.6 g, 99%) as a colourless solid. The compound is used in the next step without further purification. mp: 113-115° C.

Workup

  1. customThe excess lithium aluminum hydride was quenched with a solution of saturated sodium sulfate at 0° C
  2. filtrationThe reaction mixture was filtered
  3. washthe residue was washed with hot ethyl acetate (2×75 ml)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-daf83ead28c445b18b28d3c3facb92c8
Source dataset
uspto-grants-2008_08
Patent number
US07414128B2

Reaction notes

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