Methyl morpholine oxide → 1-(2-Chlorophenyl)-3-(methoxymethoxy)propane-1,2-diol

HRID 1506948Notes

Reaction equation

HRID 1506948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/C=C/COCOC.C[N+]1([O-])CC[O:19][CH2:18]C1.[CH3:23][C:24]([CH3:26])=[O:25].C[C:28]([OH:31])(C)C.[OH2:32]>O=[Os](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH:23]([OH:32])[CH:24]([OH:25])[CH2:26][O:19][CH2:18][O:31][CH3:28]

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 86602953Acetone tBuOH WaterHCID 90025785HCID 90025785, compound

Product 1

HCID 900190611-(2-Chlorophenyl)-3-(methoxymethoxy)propane-1,2-diolYield 70%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

(E)-1-chloro-2-(3-(methoxymethoxy)prop-1-enyl)benzene (9.1 g, Preparation Example 2) was dissolved in 45 mL of a mixture of acetone/t-BuOH/H2O (5:1:1 V/V). At room temperature, N-methylmorpholine-N-oxide (7.51 g) and OsO4 (0.54 g) were added thereto and stirred for 2-3 hours. When the reaction was completed, the obtained product was washed with water and methylenechloride (MC). Then, the organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4), filtrated, and concentrated under reduced pressure. The crude compound was purified by a silica gel column to produce the title compound (7.42 g, 70˜90%).

Workup

  1. washthe obtained product was washed with water and methylenechloride (MC)
  2. filtrationfiltrated
  3. concentrationconcentrated under reduced pressure
  4. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-23dd4a4bbfa7417ab11a7a2c0acff0b8
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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