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

HRID 966966Notes

Reaction equation

HRID 966966 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d522b5fd702d4b3e8fa054d430f241fa
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

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