Cornforth reagent → HCID 51356495, compound

HRID 2092973Notes

Reaction equation

HRID 2092973 reaction equation
[C:1]1([CH:7]([C:9]2[S:13][C:12]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:11][CH:10]=2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl.CCOC(C)=O>[C:1]1([C:7]([C:9]2[S:13][C:12]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:11][CH:10]=2)=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 58227420HCID 58227420, compound

Product 1

HCID 51356495HCID 51356495, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of phenyl-(2-phenylethynyl-thiazol-5-yl)-methanol (Example 234, 157 mg, 0.539 mmol) in dichloromethane (5.0 mL) was added pyridinium dichromate (243 mg, 0.647 mmol) and the reaction was stirred at room temperature for about 18 hours. The mixture was then diluted with EtOAc (15 mL), filtered over Celite® and washed with EtOAc. The solution was concentrated under reduced pressure and purified by preparative TLC, eluting with 20% EtOAc in hexanes, to afford the titled compound, phenyl-(2-phenylethynyl-thiazol-5-yl)-methanone (135 mg, 87%) as pale yellow oil.

Workup

  1. filtrationfiltered over Celite®
  2. washwashed with EtOAc
  3. concentrationThe solution was concentrated under reduced pressure
  4. custompurified by preparative TLC
  5. washeluting with 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-c0e57ec264314a2e827877075bd7f095
Source dataset
uspto-grants-2013_05
Patent number
US08440837B2

Reaction notes

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