Methyl morpholine oxide → HCID 67515717, compound

HRID 2173216Notes

Reaction equation

HRID 2173216 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])C=C.[CH3:12][N+]1([O-])CCOCC1.[CH3:20][OH:21].[OH2:22]>O=[Os](=O)(=O)=O>[OH:21][CH:20]([CH2:12][OH:22])[CH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 197666543-(Prop-2-en-1-yl)benzonitrileHCID 22242641Methanol--water (1/1)

Product 1

HCID 67515717HCID 67515717, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 3-(prop-2-en-1-yl)benzonitrile (3.8 g, 27 mmol) and NMO (10.85 g, 80 mmol) in MeOH/H2O (v/v=3:1, 133 mL) was added OsO4 (600 mg), and then stirred at room temperature for 18 h. The result mixture was concentrated and the residue was dissolved in water and extracted with EtOAc. The organic layers were dried and concentrated, and the residue was purified by a flash column chromatography to afford 3-(2,3-dihydroxypropyl)benzonitrile.

Workup

  1. concentrationThe result mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with EtOAc
  4. customThe organic layers were dried
  5. concentrationconcentrated
  6. customthe residue was purified by a flash column chromatography

Sources & evidence

ORD record
ord-5be0a55d451549ea8dd0866ea2897d40
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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