Methyl morpholine oxide → 1-[3,5-Bis(trifluoromethyl)phenyl]ethane-1,2-diol

HRID 966966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 966966
C([C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([C:13]([F:16])([F:15])[F:14])[CH:4]=1)=C.C[N+]1([O-])[CH2:23][CH2:22][O:21]CC1.S(=O)(O)[O-:26].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[F:14][C:13]([F:16])([F:15])[C:5]1[CH:4]=[C:3]([CH:22]([OH:21])[CH2:23][OH:26])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Komponenten

7

Edukt 3

HCID 82029Methyl morpholine oxideHCID 27732423,5-Bis(trifluoromethyl)styreneHCID 23665763Sodium Bisulfite

Produkt 1

HCID 222935121-[3,5-Bis(trifluoromethyl)phenyl]ethane-1,2-diolAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, 1 mL) was added to a mixture of 1-ethenyl-3,5-bis(trifluoromethyl)benzene (1.85 g, 7.74 mmol) and N-methylmorpholine-N-oxide (1.13 g, 9.67 mmol) in tetrahydrofuran (35 mL) and water (15 mL) and the mixture was stirred at room temperature for 18 hours. Aqueous sodium bisulfite (saturated, 30 mL) was added and the tetrahydrofuran was evaporated under reduced pressure. The mixture was extracted with ethyl acetate (2×100 mL) and the combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the title compound (2.09 g, 98%). 1H NMR (400 MHz, CDCl3) δ 7.86 (2H, s), 7.82 (1H, s), 4.97 (1H, dd, J 8.0, 4.0 Hz), 3.87 (1H, dd, J 11.0, 4.0 Hz), and 3.66 (1H, dd, J 8.0, 11.0 Hz).

Aufarbeitung

  1. customthe tetrahydrofuran was evaporated under reduced pressure
  2. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  3. dry with materialthe combined organic fractions were dried (Na2SO4)
  4. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d522b5fd702d4b3e8fa054d430f241fa
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953792B2

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