Morpholine → 4-(1-Furan-2-yl-ethyl)-morpholine

HRID 606573Notes

Reaction equation

HRID 606573 reaction equation
[C:1]([C:4]1[O:5][CH:6]=[CH:7][CH:8]=1)(=O)[CH3:2].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[O:5]1[CH:6]=[CH:7][CH:8]=[C:4]1[CH:1]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH3:2]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 145052-AcetylfuranHCID 4311764Sodium borohydride

Product 1

HCID 141200674-(1-Furan-2-yl-ethyl)-morpholineYield 14%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

2-Acetylfuran (20 mmol) and morpholine (20 mmol) were added to neat titanium isopropoxide (32 mmol) and the reaction stirred under N2 at room temperature for 3 h. Methanol (90 ml) was then added followed by the careful portionwise addition of NaBH4 (32 mmol). After stirring at room temperature for 10 mins, the reaction was quenched by addition of 0.1M NaOH and the resultant mixture filtered through a celite pad. The filtrate was extracted twice with DCM, dried over Na2SO4 and concentrated in-vacuo. Flash chromatography of the residue (silica, 5 to 20% EtOAc in Heptane) yielded pure 4-(1-furan-2-yl-ethyl)-morpholine as a golden oil: m/z in MS ES+=182 [M+H]+, 2.76 mmol, 14% yield.

Workup

  1. stirringAfter stirring at room temperature for 10 mins
  2. customthe reaction was quenched by addition of 0.1M NaOH
  3. filtrationthe resultant mixture filtered through a celite pad
  4. extractionThe filtrate was extracted twice with DCM
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-f5914a2f12a5441b97c65972b9006aae
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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