1,2-Dimethoxyethane → 5-(4-Morpholin-4-yl-phenyl)-furan-2-carbaldehyde

HRID 2197686

Reaction equation

HRID 2197686 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:14]([C:16]1[O:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>O.C(O)C>[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([C:19]3[O:20][C:16]([CH:14]=[O:15])=[CH:17][CH:18]=3)=[CH:3][CH:4]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343555-Formylfuran-2-boronic acidHCID 116228514-(4-Bromophenyl)morpholine

Product 1

HCID 594462295-(4-Morpholin-4-yl-phenyl)-furan-2-carbaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The reaction flask was flushed with nitrogen and charged with 4-(4-bromo-phenyl)-morpholine (2.134 g, 8.81 mmol), 5-formyl-furan-2-boronic acid (1.832 g, 13.10 mmol) and sodium carbonate (3.016 g, 28.46 mmol). A mixture of 1,2-dimethoxyethane (35 mL), ethanol (10 mL) and water (13 mL) was added and the reaction mixture was stirred for 10 min under a nitrogen atmosphere. Dichlorobis(triphenylphosphine) palladium(II) (0.205 g, 0.29 mmol) was added and the mixture was stirred and heated at 80° C. for 18 h. The mixture was cooled to room temperature and partitioned between ether (250 mL) and water (100 mL). The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on flash Silica (100 mL, 20% ethyl acetate in hexanes) to afford 5-(4-morpholin-4-yl-phenyl)-furan-2-carbaldehyde (1.36 g, 60%). 1H NMR (400 MHz, CDCl3): δ 3.26 (2H, dd, J=5.2, 3.6 Hz), 3.87 (2H, dd, J=5.2, 3.6 Hz), 6.69 (1H, d, J=4.0 Hz), 6.93 (2H, m), 7.26 (1H, s), 7.30 (1H, d, J=4.0), 7.74 (2H, m), 9.58 (1H, s). ESI-MS: 258.0.

Workup

  1. customThe reaction flask was flushed with nitrogen
  2. additionwas added
  3. stirringthe mixture was stirred
  4. temperatureThe mixture was cooled to room temperature
  5. custompartitioned between ether (250 mL) and water (100 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on flash Silica (100 mL, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5bf70f7e15ea404b8ff61a6bed4d18ff
Source dataset
uspto-grants-2012_12
Patent number
US08338465B2

Linked notes

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