HCID 23051862, compound → HCID 23051871, compound

HRID 1651378Notes

Reaction equation

HRID 1651378 reaction equation
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[C:5]#[C:6][CH:7]([OH:18])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:20]([O:19][CH:4]([O:3][CH2:1][CH3:2])[C:5]#[C:6][C:7](=[O:18])/[CH:8]=[CH:9]/[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[CH3:21]

Participants

4

Reactant 1

HCID 23051862HCID 23051862, compound

Product 1

HCID 23051871HCID 23051871, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.0 g (10.33 mmol) of (E)-6,6-diethoxy-1-(p-methoxyphenyl)-1-hexen-4-yn-3-ol in 15 ml of methylene chloride was added at 0° to a suspension of 27 g of manganese dioxide in 45 ml of methylene chloride. The reaction mixture was subsequently stirred at room temperature for a further 1 hour, filtered over magnesium sulphate and evaporated. The residue was chromatographed on 100 g of silica gel with petroleum ether/ether (2:1), whereupon (E)-6,6-diethoxy-1-(p-methoxyphenyl)-1-hexen-4-yn-3-one was obtained as a light yellowish oil.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. customevaporated
  3. customThe residue was chromatographed on 100 g of silica gel with petroleum ether/ether (2:1)

Sources & evidence

ORD record
ord-a26276b8c1294af0879fd32c9386f5c9
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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