HCID 23050514, compound → HCID 23050451, compound

HRID 1651786Notes

Reaction equation

HRID 1651786 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]([F:18])=[CH:14][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:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)=[O:11])[CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 23050514HCID 23050514, compound

Product 1

HCID 23050451HCID 23050451, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9.3 g (37 mmol) of 4-(1-ethoxyethoxy)-1-(4-fluorophenyl)-2-butyn-l-ol in 50 ml of methylene chloride was added dropwise at 0° to a suspension of 95 g (1.1 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-(4-fluorophenyl)-2-butyn- 1-one as an oil.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-db15acd802b142fd9e07b32cd3fbb5d4
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

Loading…