2-Methylfuran → HCID 86723490, compound

HRID 2201253Notes

Reaction equation

HRID 2201253 reaction equation
O[CH:2]1[C:10]2[N:6]([C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:8]3[C:14](=[O:15])[N:13]([CH3:16])[C:12](=[O:17])[N:11]([CH3:18])[C:9]3=2)[C@H:5]([C:25]([O:27][CH3:28])=[O:26])[CH2:4][CH2:3]1.[CH3:29][C:30]1[O:31][CH:32]=[CH:33][CH:34]=1>C(#N)C.[Au](Cl)(Cl)Cl>[CH3:18][N:11]1[C:9]2=[C:10]3[N:6]([C:7]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[C:8]2[C:14](=[O:15])[N:13]([CH3:16])[C:12]1=[O:17])[C@H:5]([C:25]([O:27][CH3:28])=[O:26])[CH2:4][CH2:3][CH:2]3[C:32]1[O:31][C:30]([CH3:29])=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 107972-MethylfuranHCID 86723489HCID 86723489, compound

Product 1

HCID 86723490HCID 86723490, compound

Reagents, catalysts & solvents 2

HCID 26030Gold trichlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

Gold (III) chloride (0.142 g, 0.469 mmol) was added to a solution of (7S)-methyl 10-hydroxy-1,3-dimethyl-2,4-dioxo-5-phenyl-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizine-7-carboxylate (1.8 g, 4.69 mmol) and 2-methylfuran (0.466 mL, 5.16 mmol) in acetonitrile (30 mL). The mixture was stirred at room temperature for 25 mins, then quenched with saturated NaHCO3(aq). The mixture was extracted with DCM, the organic phase passed through a hydrophobic frit and evaporated under vacuum.

Workup

  1. customquenched with saturated NaHCO3(aq)
  2. extractionThe mixture was extracted with DCM
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-3d4efabdb823450f87d68c5b7dcb9d60
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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