Hydrochloric Acid → HCID 23051869, compound

HRID 1651368Notes

Reaction equation

HRID 1651368 reaction equation
[OH:1][CH:2](/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:3]#[C:4][C:5]([O:7][CH3:8])=[O:6].C12CCCN=C1CCCCN2.Cl>C(Cl)Cl>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11](/[CH:10]=[CH:9]/[C:2](=[O:1])/[CH:3]=[CH:4]/[C:5]([O:7][CH3:8])=[O:6])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23051857HCID 23051857, compoundHCID 86743958HCID 86743958, compound

Product 1

HCID 23051869HCID 23051869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 20 g (8.12 mmol) of methyl (E)-4-hydroxy-6-(4-methoxyphenyl)-5-hexen-2-ynoate and 62 mg (~5 mol %) of 2,8-diazabicyclo[5.4.0]undec-7-ene in 80 ml of methylene chloride was stirred at 0° under argon for 35 hours. Thereafter, 25 ml of 0.1N hydrochloric acid were added and the phases are separated. The aqueous phase was extracted twice with 25 ml of methylene chloride. The combined organic fractions were dried over magnesium sulphate, filtered and evaporated. The residue was chromatographed on 130 g of silica gel with petroleum ether/ether (1:1), and there were obtained first methyl (E,E)-6-(4-methoxyphenyl)-4-oxo-2,5-hexadienoate of melting point 103°-103.5° and then methyl (2Z,5E)-6-(4-methoxyphenyl)-4-oxo-2,5-hexadienoate of melting point 54°-55°.

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase was extracted twice with 25 ml of methylene chloride
  3. dry with materialThe combined organic fractions were dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on 130 g of silica gel with petroleum ether/ether (1:1)

Sources & evidence

ORD record
ord-0e37c4976b7643ceb2649138c5fd6824
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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