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

HRID 1498664Notes

Reaction equation

HRID 1498664 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-8f06701c7c9347519155a261d48f88e8
Source dataset
uspto-grants-2015_12
Patent number
US09199990B2

Reaction notes

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