Diethyl Ether → HCID 21848283, compound

HRID 618717Notes

Reaction equation

HRID 618717 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]#C)[C:3]=1[CH2:12][CH2:13][CH3:14].[F-].[Cs+].[CH2:17](OCC)C>CCN(C1C=CC=CC=1)CC>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[CH:17]=[C:9]([CH3:10])[O:8][C:4]=2[C:3]=1[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 25953Cesium fluorideHCID 21848312HCID 21848312, compound

Product 1

HCID 21848283HCID 21848283, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Procedure

A suspension of 1.5 g (7.8 mmol) of 1-fluoro-2-propyl-3-prop-2-ynyloxy-benzene and 1.7 g (11.15 mmol) of caesium fluoride in 14 ml of diethylaniline was heated at reflux in a metal bath for 4 hours. After cooling to room temperature 100 ml of diethyl ether were added thereto and insoluble constituents were filtered off. The diethyl ether phase was washed three times with 60 ml of 1 N hydrochloric acid, dried over sodium sulfate and concentrated in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloromethane/hexane 1:2). There was obtained 0.6 g (40%) of 6-fluoro-2-methyl-7-propyl-benzofuran as a pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in a metal bath for 4 hours
  3. additionwere added
  4. filtrationinsoluble constituents were filtered off
  5. washThe diethyl ether phase was washed three times with 60 ml of 1 N hydrochloric acid
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in a vacuum
  8. customThe crude product obtained
  9. customwas purified by column chromatography on silica gel (dichloromethane/hexane 1:2)

Sources & evidence

ORD record
ord-905133a4c37340708de46d993c66ea67
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

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