Ethylene Glycol → (5-[1,3]-Dioxolan-2-yl-benzofuran-2-yl)-(4-fluoro-phenyl)-methanone

HRID 1171222Notes

Reaction equation

HRID 1171222 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:11]=3[CH:12]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:21](O)[CH2:22][OH:23].[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[O:18]1[CH2:21][CH2:22][O:23][CH:17]1[C:14]1[CH:15]=[CH:16][C:10]2[O:9][C:8]([C:6]([C:5]3[CH:19]=[CH:20][C:2]([F:1])=[CH:3][CH:4]=3)=[O:7])=[CH:12][C:11]=2[CH:13]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 516892Sodium BicarbonateHCID 27811012-(4-Fluorobenzoyl)-1-benzofuran-5-carbaldehyde

Product 1

HCID 68718080(5-[1,3]-Dioxolan-2-yl-benzofuran-2-yl)-(4-fluoro-phenyl)-methanoneYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(4-fluorobenzoyl)-1-benzofuran-5-carbaldehyde (500 mg, 1.86 mmol) and ethylene glycol (2.31 g, 37.2 mmol) were suspended in toluene (20 mL) followed by the addition of (1S)-(+)-10-camphorsulfonic acid (30 mg). This suspension was heated under reflux for 2 hours. After allowing the reaction mixture to cool on standing, saturated aqueous sodium bicarbonate solution was poured thereinto followed by extraction with ethyl acetate. The organic layer was separated followed by washing with sat. NaCl and drying over anhydrous magnesium sulfate. The organic layer was filtered using a glass filter and the filtrate was filtered with a glass filter coated with NH-silica gel. This filtrate was concentrated under a reduced pressure to obtain (5-[1,3]-dioxolan-2-yl-benzofuran-2-yl)-(4-fluoro-phenyl)-methanone (377 mg, 65%).

Workup

  1. temperatureThis suspension was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. extractionthereinto followed by extraction with ethyl acetate
  5. customThe organic layer was separated
  6. washby washing with sat. NaCl
  7. dry with materialdrying over anhydrous magnesium sulfate
  8. filtrationThe organic layer was filtered
  9. filtrationfilter
  10. filtrationthe filtrate was filtered with a glass
  11. filtrationfilter
  12. concentrationThis filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-218073f9907e49a18edc485fe9a27629
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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