Methyl morpholine oxide → 1-(8-Bromoquinolin-2-yl)ethane-1,2-diol

HRID 339669Notes

Reaction equation

HRID 339669 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=C(C=C)[CH:8]=[CH:7]2.C[N+]1([O-])CC[O:18]CC1.[CH3:22][C:23]([CH3:25])=[O:24].O>ClCCl.O=[Os](=O)(=O)=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:22]([CH:23]([OH:24])[CH2:25][OH:18])[CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 672347808-Bromo-2-vinylquinoline

Product 1

HCID 672345141-(8-Bromoquinolin-2-yl)ethane-1,2-diol

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 8-bromo-2-vinylquinoline (0.886 g, 3.78 mmol) in acetone/H2O (8 mL/2 mL) was added 4-methylmorpholine N-oxide (1.06 g, 4.54 mmol) followed by OsO4 (0.5 mL, 2.5% in t-BuOH). The reaction mixture was stirred for two hours at ambient temperature then diluted with dichloromethane. The organic layer was washed with saturated sodium sulfate and brine and concentrated to give crude product.

Workup

  1. washThe organic layer was washed with saturated sodium sulfate and brine
  2. concentrationconcentrated
  3. customto give crude product

Sources & evidence

ORD record
ord-83569c5c335942f6a730f427507aee7c
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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