Water → HCID 86666253, compound

HRID 533409Notes

Reaction equation

HRID 533409 reaction equation
I([O-])(=O)(=O)=O.[Na+].O.[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[C:10]=1[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=2)[C:20]([CH:31]=C)=[CH:19][N:18]=1.C1C[O:36]CC1>S([O-])([O-])=O.[Na+].[Na+].[Os](=O)(=O)(=O)=O>[CH:31]([C:20]1[C:21]2[C:26](=[CH:25][C:24]([C:27]([O:29][CH3:30])=[O:28])=[CH:23][CH:22]=2)[C:17]([C:10]2[C:9]([F:8])=[CH:14][C:13]([F:15])=[CH:12][C:11]=2[F:16])=[N:18][CH:19]=1)=[O:36]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 67774811HCID 67774811, compound

Product 1

HCID 86666253HCID 86666253, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 24437Sodium SulfiteSolvent

Procedure

Osmium tetraoxide (2.5% isobutanol solution, 0.05 mL), sodium periodate (280 mg), and water (4 mL) were added to a mixture of methyl 1-(2,4,6-trifluorophenyl)-4-vinylisoquinoline-7-carboxylate (180 mg) and THF (4 mL), followed by stirring at room temperature for 12 hours. The reaction mixture was diluted with an aqueous sodium sulfite solution, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 4-formyl-1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylate (153 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. custompurified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b65653e6fe2642358010b3ec40714834
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

Loading…