HCID 23050489, compound → HCID 23050482, compound

HRID 1651781Notes

Reaction equation

HRID 1651781 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]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[C:13]=1[O:22][CH3:23])[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]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[C:13]=1[O:22][CH3:23])=[O:11])[CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 23050489HCID 23050489, compound

Product 1

HCID 23050482HCID 23050482, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 12 g (37 mmol) of 4-(1-ethoxyethoxy)-1-(2,3,4-trimethoxyphenyl)-2-butyn-1-ol in 50 ml of methylene chloride was added dropwise at 0° to a suspension of 95.3 g (1.1 mol) of manganese dioxide in 150 ml of methylene chloride. The reaction mixture was stirred at 0° for 15 minutes, filtered over magnesium sulphate and concentrated. Chromatography of the residue over 300 g of silica gel (elution agent ether/hexane 1:1) yielded 4-(1-ethoxyethoxy)-1-(2,3,4-trimethoxyphenyl)-2-butyn-1-one as a yellow oil.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-90d13560826f406eb2536c41a97c0e14
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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