Sodium Bicarbonate → HCID 20164615, compound

HRID 255839Notes

Reaction equation

HRID 255839 reaction equation
C(O[CH:4]([O:25]CC)[C:5]#[C:6][C:7]([CH:15]([CH3:24])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)O)C.C(=O)(O)[O-:29].[Na+]>S(=O)(=O)(O)O>[Cl:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[CH:15]([C:7]1([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[C:6](=[O:29])[CH:5]=[CH:4][O:25]1)[CH3:24]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20164656HCID 20164656, compound

Product 1

HCID 20164615HCID 20164615, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1 g of α-(3,3-diethoxy-1-propynyl)-α-(2,4-dichloro-α-methylbenzyl)-3-pyridinemethanol in 30 ml of 4N sulphuric acid is heated at 120° C. for 1.5 hours while stirring and the reaction mixture is subsequently left to cool to room temperature, neutralized with solid sodium bicarbonate and extracted with methylene chloride. The organic phase is washed three times with saturated aqueous sodium chloride solution and evaporated under reduced pressure. Thereafter, the residue is subjected to a column chromatography on silica gel using methylene chloride/ethyl acetate (4:1) as the eluent and it is recrystallized from n-hexane. In this manner there is obtained 0.4 g of 2-(2,4-dichloro-α-methylbenzyl)-2-(3-pyridyl)-3(2H)-furanone, m.p. 111°-111.5° C.

Workup

  1. waitthe reaction mixture is subsequently left
  2. extractionextracted with methylene chloride
  3. washThe organic phase is washed three times with saturated aqueous sodium chloride solution
  4. customevaporated under reduced pressure
  5. customis recrystallized from n-hexane

Sources & evidence

ORD record
ord-fddcde6d617642b7bfc6283ba81fd145
Source dataset
uspto-grants-1987_10
Patent number
US04699652

Reaction notes

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