Water → HCID 46941771, compound

HRID 2091088Notes

Reaction equation

HRID 2091088 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1.[CH:12]1([C:17](Cl)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1.[Cl-].[Al+3].[Cl-].[Cl-].O>[N+](C)([O-])=O>[CH:12]1([C:17]([C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:11][C:6]=3[C:7]=2[CH3:10])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 78284Cyclopentanecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 116798475-Fluoro-3-methylbenzofuran

Product 1

HCID 46941771HCID 46941771, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a solution of 5-fluoro-3-methyl-1-benzofuran (2.0 g) synthesized above, cyclopentanecarbonylchloride (1.94 g) in nitromethane (40 mL) was added aluminum chloride (anhydrous) (2.66 g) at 0° C., and the mixture was stirred for 3 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate 100:0-95:5, v/v) to give the title compound (2.11 g, 64%) as a colorless amorphous form.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9e03ab982a064270819d27f565bec3df
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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