tert-Butanol → HCID 58592731, compound

HRID 642853Notes

Reaction equation

HRID 642853 reaction equation
[F:1][C:2]([F:17])([F:16])[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=C)=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])[F:5].CC([OH:22])(C)C>O1CCOCC1.O.O=[Os](=O)(=O)=O>[F:1][C:2]([F:17])([F:16])[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:22])=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 2

HCID 6386tert-ButanolHCID 225064851-(2,2,2-Trifluoro-1-trifluoromethyl-ethyl)-4-vinyl-benzene

Product 1

HCID 58592731HCID 58592731, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-(2,2,2-Trifluoro-1-trifluoromethyl-ethyl)-4-vinyl-benzene (80 mg, 0.3 mmol) was dissolved in dioxane (6 ml) and water (5 ml). NaIO4 (181 mg, 0.84 mmol) and OsO4 (0.18 ml of a 2.5 % t-BuOH solution) were added. The mixture was allowed to stir at room temperature for 2 h, and then it was partitioned between ethyl acetate and brine. The ethyl acetate was washed with three additional times with brine, dried over MgSO4, and the solvent was removed under vacuum to give the title product (47 mg (61%), 0.18 mmol). 1H NMR (CDCl3): δ=10.08 (s, 1H), 8.04 (d, J=8.3 Hz, 2H), 7.76 (d, J=8.3 Hz, 2H), 5.82 (m, 1H).

Workup

  1. customit was partitioned between ethyl acetate and brine
  2. washThe ethyl acetate was washed with three additional times with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-3dd58389c88247ec955cedf99015ced5
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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