Sodium Hydroxide → 3-[(2S)-oxiran-2-yl]pyridine

HRID 1819445Notes

Reaction equation

HRID 1819445 reaction equation
Br[CH2:2][C@H:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[OH:4].[OH-].[Na+]>C1COCC1>[O:4]1[CH2:2][C@@H:3]1[C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57885768(S)-2-bromo-1-pyridin-3-yl-ethanol

Product 1

HCID 133195603-[(2S)-oxiran-2-yl]pyridineYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-Bromo-1-pyridin-3-yl-ethanol (134 mg, 0.66 mmol) in THF (10 mL) was added 4N NaOH solution (8.3 mL). The reaction mixture was stirred at room temperature for 1 h. The organic phase was separated, dried over Na2SO4 and concentrated. Silica gel prep TLC of the resulting residue using 99:1 CH2Cl2:MeOH as an eluant afforded 34 mg of (S)-3-Oxiranyl-pyridine as a colorless oil (42%).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a478ff4d438946af879000b2c0cbcb3e
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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