HCID 70199009, compound → HCID 53926227, compound

HRID 342418Notes

Reaction equation

HRID 342418 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[O:11][C:10]2[C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:9]=2[CH:8]=1)([OH:3])=O>S(Cl)(Cl)=O.C1(C)C=CC=CC=1>[N+:16]([C:12]1[C:10]2[O:11][C:7]3[CH2:6][CH2:5][CH2:4][C:1](=[O:3])[C:8]=3[C:9]=2[CH:15]=[CH:14][CH:13]=1)([O-:18])=[O:17]

Participants

4

Reactant 1

HCID 70199009HCID 70199009, compound

Product 1

HCID 53926227HCID 53926227, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-(3-carboxypropyl)-7-nitrobenzo[b]furan (500 mg) in thionyl chloride (5 ml) was refluxed for 1.5 hours. The reaction mixture was diluted with toluene and concentrated in vacuo. The residue was dissolved in dichloromethane (15 ml) and to the mixture was added aluminum chloride (435 mg) at 4° C. The mixture was stirred at ambient temperature for 2 hours and partitioned between 1N-hydrochloric acid and dichloromethane. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from a mixture of ethyl acetate and n-hexane to give 6-nitro-1-oxo-1,2,3,4-tetrahydrodibenzofuran (282 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (15 ml) and to the mixture
  3. additionwas added aluminum chloride (435 mg) at 4° C
  4. custompartitioned between 1N-hydrochloric acid and dichloromethane
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel
  10. customthe obtained oil was crystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-a0c24caafb5541d3a8ee45d2e0fae23b
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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