2-Morpholinoethanol → 3,5-Dimethyl-4-(2-morpholin-4-yl-ethoxy)benzaldehyde

HRID 336680Notes

Reaction equation

HRID 336680 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:11].O[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(OCC)(=O)C>[CH3:10][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([CH3:11])[C:2]=1[O:1][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[CH:6]=[O:7]

Participants

7

Reactant 4

HCID 611632-MorpholinoethanolHCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 81531DiisopropylethylamineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 289325803,5-Dimethyl-4-(2-morpholin-4-yl-ethoxy)benzaldehydeYield 32%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-3,5-dimethyl benzaldehyde (3.0 g, 20 mmol) in anhydrous THF (100 mL), triphenyl phosphene (10.49 g, 40 mmol), 4-(2-hydroxyethyl)morpholine (5.25 g, 40 mmol) and N,N-diisopropylethylamine (7.76 g, 60 mmol) were added. To this stirred solution was added diethylazodicarboxylate (6.97 g, 40 mmol). The reaction mixture was stirred at room temperature overnight under nitrogen and diluted with ethyl acetate (200 mL). The organic layer was washed with water and brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The crude material was purified by column chromatography (silica gel 230-400 mesh; 0-3% methanol in CH2Cl2 as eluent) to give 3,5-dimethyl-4-(2-morpholin-4-yl-ethoxy) benzaldehyde (1.66 g, 32%) as an oil.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. customThe crude material was purified by column chromatography (silica gel 230-400 mesh; 0-3% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-b035851d49824ecfb9b23941966f375d
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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