phosphorous acid, trisodium salt → 5-Cyclopropoxy-2-methylpyridine

HRID 1690201

Reaction equation

HRID 1690201 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2(S(C3C=CC=CC=3)(=O)=O)[CH2:11][CH2:10]2)=[CH:4][N:3]=1.P([O-])([O-])[O-].[Na+].[Na+].[Na+].C(=O)([O-])O.[Na+]>CO>[CH:9]1([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][CH:4]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 134681phosphorous acid, trisodium saltHCID 516892Sodium BicarbonateHCID 665983222-Methyl-5-[1-(phenylsulfonyl)cyclopropoxy]pyridine

Product 1

HCID 585206415-Cyclopropoxy-2-methylpyridineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methyl-5-(1-(phenylsulfonyl)cyclopropoxy)pyridine (540 mg, 1.87 mmol) was dissolved in methanol (5.5 mL), and sodium phosphite (671 mg, 5.598 mmol) and amalgam sodium (3.58 g, 7.47 mmol) were added thereto under ice-cold conditions, and the resultant mixture was stirred at the same temperature for 30 minutes, and then further stirred at room temperature for 3 hours. The reaction solution was added with a saturated aqueous solution of sodium hydrogen carbonate and extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by distillation, and 5-cyclopropoxy-2-methylpyridine (240 mg, yield 86%) was obtained as a yellow oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. distillationThe obtained residue was purified by distillation

Sources & evidence

ORD record
ord-f3d2aeb508bf473f89d6f27ec3af9a60
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Linked notes

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