Aluminium lithium hydride → HCID 67042011, compound

HRID 716981Notes

Reaction equation

HRID 716981 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][N:14]2[CH:19]([CH3:20])[CH2:18][O:17][CH2:16][C:15]2=O)=[CH:11][CH:10]=1>O1CCCC1.O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH:19]2[CH3:20])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22289846HCID 22289846, compound

Product 1

HCID 67042011HCID 67042011, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of LiAlH4 (3.83 g, 100.79 mmol, 2.00 equiv) in tetrahydrofuran (100 mL). This was followed by the addition of a solution of 4-(4-methoxybenzyl)-5-methylmorpholin-3-one (11.9 g, 50.42 mmol, 1.00 equiv) in tetrahydrofuran (50 mL) dropwise with stirring at 0° C. The resulting solution was heated to reflux for 1 h in an oil bath and cooled to room temperature. The resulting solution was diluted with 100 mL of H2O. The resulting solution was extracted with 3×200 mL of ethyl acetate and the organic layers combined and dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30). This resulted in 7 g (58%) of 4-(4-methoxybenzyl)-3-methylmorpholine as yellow oil.

Workup

  1. customInto a 250-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 1 h in an oil bath
  5. temperaturecooled to room temperature
  6. extractionThe resulting solution was extracted with 3×200 mL of ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customThis resulted in 7 g (58%) of 4-(4-methoxybenzyl)-3-methylmorpholine as yellow oil

Sources & evidence

ORD record
ord-a7799cce09364b979b08d44abdb23a61
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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