Sodium hydride → HCID 22289846, compound

HRID 1405545Notes

Reaction equation

HRID 1405545 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][N:10]([CH:15]([CH3:18])[CH2:16][OH:17])[C:11](=[O:14])[CH2:12]Br)=[CH:7][CH:6]=1>O1CCCC1>[CH3:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][N:10]2[CH:15]([CH3:18])[CH2:16][O:17][CH2:12][C:11]2=[O:14])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67041745HCID 67041745, compound

Product 1

HCID 22289846HCID 22289846, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of sodium hydride (3.46 g, 100.92 mmol, 2.00 equiv, 70%) in tetrahydrofuran (200 mL). This was followed by the dropwise addition of a solution of N-(4-methoxybenzyl)-2-bromo-N-(1-hydroxypropan-2-yl)acetamide (16 g, 50.47 mmol, 1.00 equiv) in tetrahydrofuran (100 mL) with stirring at 25° C. The resulting solution was stirred overnight at 25° C. in an oil bath. The reaction was then quenched by the addition of 200 g of water/ice. The resulting solution was extracted with 5×200 mL of dichloromethane and the organic layers combined. The organic layers were washed with 3×50 mL of H2O. Dried over anhydrous magnesium sulfate and concentrated under vacuum. This resulted in 11.9 g (crude) of 4-(4-methoxybenzyl)-5-methylmorpholin-3-one as yellow oil.

Workup

  1. customInto a 500-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred overnight at 25° C. in an oil bath
  4. customThe reaction was then quenched by the addition of 200 g of water/ice
  5. extractionThe resulting solution was extracted with 5×200 mL of dichloromethane
  6. washThe organic layers were washed with 3×50 mL of H2O
  7. dry with materialDried over anhydrous magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customThis resulted in 11.9 g (crude) of 4-(4-methoxybenzyl)-5-methylmorpholin-3-one as yellow oil

Sources & evidence

ORD record
ord-f263d8c7929e469496ccefa3dec14ed1
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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