1-phenyl-5-(1-phenyl-1H-pyrazol-5-yl)penta-1,4-diyn-3-ol → 1-phenyl-5-(1-phenyl-1H-pyrazol-5-yl)penta-1,4-diyn-3-one

HRID 1747827Notes

Reaction equation

HRID 1747827 reaction equation
[C:1]1([C:7]#[C:8][CH:9]([OH:23])[C:10]#[C:11][C:12]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>ClCCl.[O-2].[O-2].[Mn+4]>[C:1]1([C:7]#[C:8][C:9](=[O:23])[C:10]#[C:11][C:12]2[N:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 895864351-phenyl-5-(1-phenyl-1H-pyrazol-5-yl)penta-1,4-diyn-3-ol

Product 1

HCID 895861451-phenyl-5-(1-phenyl-1H-pyrazol-5-yl)penta-1,4-diyn-3-oneYield 62.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-phenyl-5-(1-phenyl-1H-pyrazol-5-yl)penta-1,4-diyn-3-ol (0.50 g) in dichloromethane (20.0 mL) was added manganese dioxide (0.438 g), and the mixture was heated under reflux for 2 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane) to give the title compound (0.310 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-c81666c7b4bf4fa88a26ffbf8868fad2
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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