Diethyl Ether → 2-Methyl-5-(3-methyloxetan-3-yl)phenol

HRID 80758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 80758
[Mg].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:13]S(C3C=CC=CC=3)(=O)=O)[CH2:12][O:11][CH2:10]2)=[CH:5][C:4]=1[OH:23].CCOCC>CO>[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:13])[CH2:10][O:11][CH2:12]2)=[CH:5][C:4]=1[OH:23]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 5462224MagnesiumHCID 712389972-Methyl-5-(3-((phenylsulfonyl)methyl)oxetan-3-yl)phenol

Produkt 1

HCID 866902492-Methyl-5-(3-methyloxetan-3-yl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Magnesium (granulate) (8.70 g, 358 mmol) was added to a solution of crude 2-methyl-5-(3-((phenylsulfonyl)methyl)oxetan-3-yl)phenol (7.6 g, 23.9 mmol) in MeOH (100 mL). The resulting mixture was stirred for 2 min in an ultrasound bath. The flask was then fitted with a condenser. Stirring was continued for 3 h, at which point the reaction mixture turned cloudy and off white in color. The reaction was exothermic, which caused the solvent to reflux. Water bath was added to lower the reaction mixture temperature to room temperature. The reaction mixture was then stirred overnight and became heterogeneous and pale orange in color. Et2O (525 mL) was added, followed by Na2SO4.10H2O (85 g). The resulting mixture was stirred for 2 h at room temperature and Celite® was then added. The resulting mixture was stirred for another 1 h and filtered through a Buchner funnel packed with Celite®. The cake was washed with EtOAc (2×) and MeOH (1×). The light yellow filtrate was concentrated and the residue was triturated with CHCl3 (220 mL) and filtered. The filtrate was concentrated to provide 2-methyl-5-(3-methyloxetan-3-yl)phenol. 1H NMR (400 MHz, CD2Cl2) δ ppm 7.14 (d, J=7.83 Hz, 1 H) 6.73 (d, J=7.58 Hz, 1 H) 6.69 (d, J=1.77 Hz, 1 H) 4.92 (d, J=5.31 Hz, 2 H) 4.61 (d, J=5.56 Hz, 2 H) 2.26 (s, 3 H) 1.72 (s, 3 H)

Aufarbeitung

  1. customThe flask was then fitted with a condenser
  2. stirringStirring
  3. waitwas continued for 3 h, at which
  4. temperatureto reflux
  5. additionWater bath was added
  6. customto room temperature
  7. stirringThe reaction mixture was then stirred overnight
  8. stirringThe resulting mixture was stirred for 2 h at room temperature
  9. additionCelite® was then added
  10. stirringThe resulting mixture was stirred for another 1 h
  11. filtrationfiltered through a Buchner funnel
  12. washThe cake was washed with EtOAc (2×) and MeOH (1×)
  13. concentrationThe light yellow filtrate was concentrated
  14. customthe residue was triturated with CHCl3 (220 mL)
  15. filtrationfiltered
  16. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-bf76386d5e684773a617cefdde1c9f8b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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