Water → HCID 68594554, compound

HRID 1910400Notes

Reaction equation

HRID 1910400 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][C:16]([C:25](OCC)=[O:26])([C:20](OCC)=[O:21])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][C:16]([CH2:20][OH:21])([CH2:25][OH:26])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68534910HCID 68534910, compound

Product 1

HCID 68594554HCID 68594554, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring suspension of lithium aluminum hydride (8.49 g) in THF (500 ml) was added diethyl 4-benzyl-3-oxomorpholine-2,2-dicarboxylate (25 g) under ice-cooled bath, and the mixture was stirred for 1 hour at room temperature. Then the whole was warmed up to 65° C. (inner temperature), and the mixture was stirred for 2 hours. The whole was cooled with ice-cooled bath, and water (8.5 ml) was added dropwise to the mixture. The whole was stirred for 15 minutes. 4 N NaOH (8.5 ml) was added to the mixture, and the whole was stirred for 15 minutes. Then water (25.5 ml) was added again to the mixture and the whole was stirred for 1 hour at room temperature. The white precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in diisopropyl ether, and tritulated to yield white solid, which was collected by filteration to give (4-benzylmorpholine-2,2-diyl)dimethanol (10.3 g).

Workup

  1. temperaturecooled bath
  2. temperatureThen the whole was warmed up to 65° C. (inner temperature)
  3. stirringthe mixture was stirred for 2 hours
  4. temperatureThe whole was cooled with ice-
  5. temperaturecooled bath
  6. stirringThe whole was stirred for 15 minutes
  7. stirringthe whole was stirred for 15 minutes
  8. stirringthe whole was stirred for 1 hour at room temperature
  9. filtrationThe white precipitate was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. dissolutionThe residue was dissolved in diisopropyl ether
  12. customto yield white solid, which
  13. customwas collected by filteration

Sources & evidence

ORD record
ord-3b4c7d0c94874949b70fdf51afd2e6a1
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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