HCID 23050461, compound → HCID 23050508, compound

HRID 1651789Notes

Reaction equation

HRID 1651789 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH2:7][C:8]#[C:9][CH:10]([C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)[OH:11])[CH3:5])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:3][CH:4]([O:6][CH2:7][C:8]#[C:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)=[O:11])[CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 23050461HCID 23050461, compound

Product 1

HCID 23050508HCID 23050508, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.9 g 39.2 mmol) of 4-(1-ethoxyethoxy)-1-[3,4-(methylenedioxy)phenyl]-2-butyn-1-ol in 63 ml of methylene chloride was added dropwise at 0° to a suspension of 101 g (1.16 mol) of manganese dioxide in 150 ml of methylene chloride. The reaction mixture was stirred at 0° for 10 minutes, filtered over magnesium sulphate and concentrated. Chromatography of the residue on 300 g of silica gel (elution agent ether/hexane 1:1) yielded 4-(1-ethoxyethoxy)-1-[3,4 -(methylenedioxy)phenyl]2-butyn-1-one as an oil.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a59d6045ca19423ab61f494ca16439f9
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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