HCID 86743960, compound → HCID 86743961, compound

HRID 1651372Notes

Reaction equation

HRID 1651372 reaction equation
[OH:1][CH:2](/[CH:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:3]#[C:4][C:5]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:6]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17](/[CH:16]=[CH:15]/[C:2](=[O:1])[C:3]#[C:4][C:5]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:6])=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 86743960HCID 86743960, compound

Product 1

HCID 86743961HCID 86743961, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.4 g (7.2 mmol) of 2-(2-methoxyethoxy)-ethyl (E)-4-hydroxy-6-(4-methoxyphenyl)-5-hexen-2-ynoate in 40 ml of methylene chloride was added dropwise at 0° to a suspension of 9.4 g (108 mmol) of manganese dioxide in 30 ml of methylene chloride. The reaction mixture was stirred at 0° for 2 hours, filtered over magnesium sulphate and concentrated. Crystallization of the residue from ether/hexane yielded 2-(2-methoxyethoxy)ethyl (E)-6-(4-methoxyphenyl)-4-oxo-5-hexen-2-ynoate of melting point 41°-42°.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated
  3. customCrystallization of the residue from ether/hexane

Sources & evidence

ORD record
ord-a38dc15e9ce34b3aac726f5776ac0d2a
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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