Methanol → 4-Benzyl-2-(2-methyl-1,3-dioxolan-2-yl)morpholine

HRID 1029665Notes

Reaction equation

HRID 1029665 reaction equation
[CH2:1]([N:8]1[C:13](=O)[CH2:12][O:11][CH:10]([C:15]2([CH3:20])[O:19][CH2:18][CH2:17][O:16]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O.C(OCC)(=O)C>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:15]2([CH3:20])[O:16][CH2:17][CH2:18][O:19]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8857Ethyl AcetateHCID 151173024-Benzyl-2-(2-methyl-1,3-dioxolan-2-yl)-5-oxomorpholine

Product 1

HCID 151173034-Benzyl-2-(2-methyl-1,3-dioxolan-2-yl)morpholineYield 45.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethyl sulfide complex (2.2 ml) was added to a solution of 4-benzyl-2-(2-methyl-1,3-dioxolan-2-yl)-5-oxomorpholine (4.6 g) in tetrahydrofuran (60 ml) under ice-cooling. The mixture was stirred at ambient temperature for 40 hours and methanol (5 ml) was added to the mixture. After 2 hours, the mixture was concentrated under reduced pressure to give a syrup. The syrup was poured into a mixture of water (100 ml) and ethyl acetate (100 ml). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (50 g) and eluted with chloroform to give 4-benzyl-2-(2-methyl-1,3-dioxolan-2-yl)morpholine (2.00 g) as a syrup.

Workup

  1. temperaturecooling
  2. waitAfter 2 hours
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customto give a syrup
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a syrup
  9. washeluted with chloroform

Sources & evidence

ORD record
ord-885878ff11d6418a943c9bf2850ef4d7
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

Loading…