Water → HCID 66777284, compound

HRID 2091091Notes

Reaction equation

HRID 2091091 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.[CH2:12]([CH:14]([CH2:18][CH3:19])[C:15](Cl)=[O:16])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].O>[N+](C)([O-])=O>[CH2:12]([CH:14]([CH2:18][CH3:19])[C:15]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:11][C:6]=2[C:7]=1[CH3:10])=[O:16])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 759542-Ethylbutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 116798475-Fluoro-3-methylbenzofuran

Product 1

HCID 66777284HCID 66777284, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a solution of 5-fluoro-3-methyl-1-benzofuran (12.0 g) synthesized in Example A67(2), 2-ethylbutyrylchloride (9.58 g) in nitromethane (240 mL) was added aluminum chloride (anhydrous) (12.94 g) at 0° C., and the mixture was stirred for 1.5 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 100:0-90:10, v/v) to give the title compound (15.02 g, 93%) as a yellow oil.

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-49e4344eedf34188ae45ef0adea5e1bc
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…