Water → HCID 555716, compound

HRID 899259Notes

Reaction equation

HRID 899259 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1C=C.C[N+]1([O-])[CH2:16][CH2:15][O:14]CC1.[OH2:18]>C(#N)C.CC(O)(C)C.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:15]([OH:14])[CH2:16][OH:18]

Participants

7

Reactant 3

HCID 962WaterHCID 162642-BromostyreneHCID 82029Methyl morpholine oxide

Product 1

HCID 555716HCID 555716, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of 1-bromo-2-vinylbenzene (4.14 g, 22.6 mmol) and 4-methylmorpholine N-oxide in acetonitrile (20 mL) and water (10 mL) was added a 2.5% solution of osmium tetroxide in 2-methyl-2-propanol (2 mL) at room temperature and the mixture was stirred for 24 h at the same temperature. The reaction mixture was quenched by the addition of sodium hydrosulfate, and diluted with water, then extracted with ethyl acetate. The organic layer washed with diluted hydrochloric acid aqueous solution and brine, dried over sodium sulfate, and evaporated to afford 5.01 g (quant.) of the title compound as a brown solid:

Workup

  1. customThe reaction mixture was quenched by the addition of sodium hydrosulfate
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer washed with diluted hydrochloric acid aqueous solution and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-076fae4a1dce4a5eb229f917331f14ce
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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