Diethyl Ether → HCID 19926473, compound

HRID 1647163Notes

Reaction equation

HRID 1647163 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:10][CH2:11][OH:12].[H-].[Na+].C(OCC)C>C1COCC1>[CH2:10]1[CH2:11][O:12][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=2[O:9]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 54170165HCID 54170165, compound

Product 1

HCID 19926473HCID 19926473, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-chloro-3-hydroxyethoxy-2-methylpyridine (1.03g, 0.0055 mol) and NaH (55% in oil, 599 mg, 0.0138 mol) in 600 ml THF was refluxed for 15 h. Excess NaH was destroyed with 3 ml of H2O. The solvent was evaporated and the residue partitioned between 100 ml 1M HCl and 100 ml CH2Cl2. The aqueous layer was collected, washed once more with 100 ml CH2Cl2 and then treated with Na2CO3 until the pH was ≈10. The aqueous layer was extracted with 150+100 ml CH2Cl2. The two latter organic layers were combined, dried over MgSO4, and evaporated leaving 720 mg enriched product. Chromatography (silica gel, diethyl ether) furnished 0.49 g (59%) pure product.

Workup

  1. temperaturewas refluxed for 15 h
  2. customExcess NaH was destroyed with 3 ml of H2O
  3. customThe solvent was evaporated
  4. customthe residue partitioned between 100 ml 1M HCl and 100 ml CH2Cl2
  5. customThe aqueous layer was collected
  6. washwashed once more with 100 ml CH2Cl2
  7. additiontreated with Na2CO3 until the pH was ≈10
  8. extractionThe aqueous layer was extracted with 150+100 ml CH2Cl2
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. customleaving 720 mg

Sources & evidence

ORD record
ord-e4f0fb4d02ac4fe6a56be9d2dba0602d
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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