Hydrochloric Acid → HCID 20164696, compound

HRID 255840Notes

Reaction equation

HRID 255840 reaction equation
C([O:3][C:4]([C:6]([CH:14]([CH2:23][C:24]#[CH:25])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[OH:7])=[CH2:5])C.Cl>CO>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH:14]([CH2:23][C:24]#[CH:25])[C:6]([OH:7])([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:4](=[O:3])[CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20164645HCID 20164645, compound

Product 1

HCID 20164696HCID 20164696, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.0 g of α-(1-ethoxyvinyl)-α-[2,4-dichloro-α-(2-propynyl)-benzyl]-3-pyridinemethanol (see Example 3, 1st end product), 1 ml of concentrated hydrochloric acid and 15 ml of methanol as a clear yellow solution is held at room temperature for 1 hour. Thereafter, the mixture is evaporated under reduced pressure in order to remove methanol and the residue is neutralized with saturated aqueous sodium bicarbonate solution. The aqueous mixture is extracted with ethyl acetate and the organic phase is washed with saturated aqueous sodium chloride solution and evaporated. Finally, the residue is recrystallized from methylene chloride/n-hexane. There are obtained 1.8 g of 4-(2,4-dichlorophenyl)-3-hydroxy-3-(3-pyridyl)-6-heptyn-2-one, m.p. 132° C.

Workup

  1. customThereafter, the mixture is evaporated under reduced pressure in order
  2. customto remove methanol
  3. extractionThe aqueous mixture is extracted with ethyl acetate
  4. washthe organic phase is washed with saturated aqueous sodium chloride solution
  5. customevaporated
  6. customFinally, the residue is recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-f4efa9d6aa6846789db741a00ed5ed54
Source dataset
uspto-grants-1987_10
Patent number
US04699652

Reaction notes

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