Ethanol → 5-(4-Isobutyl-phenyl)-furan-2-carbaldehyde

HRID 2197672Notes

Reaction equation

HRID 2197672 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:18](O)[CH3:19].O.[CH3:22][O:23][CH2:24][CH2:25][O:26]C>CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:8]([C:5]1[CH:6]=[CH:7][C:2]([C:22]2[O:23][C:24]([CH:25]=[O:26])=[CH:19][CH:18]=2)=[CH:3][CH:4]=1)[CH:9]([CH3:11])[CH3:10]

Participants

8

Reactant 5

HCID 702EthanolHCID 962WaterHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 37890181-Bromo-4-(2-methylpropyl)benzene

Product 1

HCID 594462265-(4-Isobutyl-phenyl)-furan-2-carbaldehydeYield 31%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-bromo-4-isobutylbenzene (1.500 g, 7.04 mmol), 5-formyl-2-furanoboronic acid (1.477, 10.56 mmol) and sodium carbonate (3.134 g, 29.57 mmol) in a mixture of 1,2-dimethoxyethane (75 mL), ethanol (30 mL) and water (15 mL) was vigorously stirred and the reaction flask was purged with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.404 g, 0.35 mmol) was added and the reaction mixture was heated at 60° C. for 3 h. The mixture was allowed to cool to room temperature and was left aside for 4 days. The reaction mixture was diluted with ether (200 mL) and washed successively with water (2×100 mL) and brine. The organic layer was separated, dried over sodium sulfate and concentrated. The residue was chromatographed on flash Silica, eluted with 5 to 10% ethyl acetate in hexanes to afford 5-(4-isobutyl-phenyl)-furan-2-carbaldehyde (490 mg, 31%). 1H NMR (400 MHz, CDCl3): 0.92 (6H, d, J=6.4 Hz), 1.90 (1H, m), 2.51 (2H, d, J=7.2 Hz), 6.80 (1H, d, J=3.6 Hz), 7.20 (2H, m), 7.31 (1H, dd, J=3.6, 1.2 Hz), 7.74 (2H, m), 9.63 (1H, s). ESI-MS: 227.1.

Workup

  1. customthe reaction flask was purged with nitrogen
  2. temperatureto cool to room temperature
  3. washwashed successively with water (2×100 mL) and brine
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on flash Silica
  8. washeluted with 5 to 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e0dcab46b99b45e7bcbf90cf481550f4
Source dataset
uspto-grants-2012_12
Patent number
US08338465B2

Reaction notes

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