Tetrahydrofuran → HCID 66868239, compound

HRID 1909857Notes

Reaction equation

HRID 1909857 reaction equation
[Br-].[O:2]=[C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:4]1.O1CCCC1.CC(C)([O-])C.[K+].[Cl:42][C:43]1[CH:44]=[CH:45][C:46]([N+:51]([O-:53])=[O:52])=[C:47]([CH:50]=1)[CH:48]=O>O>[Cl:42][C:43]1[CH:44]=[CH:45][C:46]([N+:51]([O-:53])=[O:52])=[C:47]([CH:50]=1)[CH:48]=[C:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:3](=[O:2])[O:4]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 811235-Chloro-2-nitrobenzaldehydeHCID 19988374HCID 19988374, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 66868239HCID 66868239, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (3-oxo-1,3-dihydro-2-benzofuran-1-yl)(triphenyl) phosphonium bromide (5.1 g) and tetrahydrofuran (50 mL) were added potassium tert-butoxide (1.3 g) and 5-chloro-2-nitro benzoaldehyde (1.0 g) at room temperature under an argon atmosphere, followed by stirring for 5 minutes. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 3-(5-chloro-2-nitrobenzylidene)-2-benzofuran-1(3H)-one (808 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0a7be9bcdac04d308ed733918b1eda8f
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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