1,2-Dimethoxyethane → 5-(5-Tert-butyl-2-hydroxy-phenyl)-furan-2-carbaldehyde

HRID 2197678

Reaktionsgleichung

Reaktionsgleichung von HRID 2197678
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:12].[CH:13]([C:15]1[O:19][C:18](B(O)O)=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C(OC)(C)(C)C.O>[C:8]([C:6]1[CH:5]=[CH:4][C:3]([OH:12])=[C:2]([C:18]2[O:19][C:15]([CH:13]=[O:14])=[CH:16][CH:17]=2)[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 751472-Bromo-4-tert-butylphenolHCID 27343555-Formylfuran-2-boronic acid

Produkt 1

HCID 594462335-(5-Tert-butyl-2-hydroxy-phenyl)-furan-2-carbaldehydeAusbeute 7,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A reaction flask was flushed with nitrogen and charged with 2-bromo-4-tert-butyl-phenol (2.019 g, 8.81 mmol), 5-formyl-furan-2-boronic acid (1.831 g, 13.09 mmol) and sodium carbonate (2.783 g, 26.26 mmol). A mixture of 1,2-dimethoxyethane (40 mL) and water (13 mL) was added and the reaction mixture was stirred for 10 min under a nitrogen atmosphere. Dichlorobis(triphenylphosphine) palladium(II) (0.193 g, 0.27 mmol) was added and the mixture was stirred and heated to 65° C. for 17 h. The mixture was cooled to room temperature, diluted with methyl tert-butyl ether (MTBE) (250 mL) and washed successively with 5% aq. potassium carbonate (100 mL), water (100 mL) and brine. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on flash Silica (100 g, 5 to 10% ethyl acetate in hexanes) to afford 5-(5-tert-butyl-2-hydroxy-phenyl)-furan-2-carbaldehyde (160 mg, 7%). 1H NMR (400 MHz, CDCl3): δ 1.33 (9H, s) 6.51 (1H, bs), 6.90 (1H, d, J=8.8 Hz), 7.03 (1H, d, J=4.0 Hz), 7.32 (1H, dd, J=8.8, 2.4 Hz), 7.36 (1H, d, J=3.6 Hz), 7.73 (1H, d, J=3.2 Hz), 9.64 (1H, s). ESI-MS: 243.0.

Aufarbeitung

  1. customA reaction flask was flushed with nitrogen
  2. additionwas added
  3. stirringthe mixture was stirred
  4. temperatureThe mixture was cooled to room temperature
  5. washwashed successively with 5% aq. potassium carbonate (100 mL), water (100 mL) and brine
  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 g, 5 to 10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4dbd7c118c414e649b114972156dc15e
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338465B2

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