HCID 23050489, compound → HCID 23050482, compound
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
Product 1
Reagents, catalysts & solvents 2
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.