HCID 59051257, compound → HCID 86643254, compound

HRID 1692639Notes

Reaction equation

HRID 1692639 reaction equation
[O:1]=[C:2]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C:4]2[C:13]([C:17](O)=[O:18])=[CH:14][CH:15]=[CH:16][C:3]1=2.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:1]=[C:2]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C:4]2[C:13]([CH:17]=[O:18])=[CH:14][CH:15]=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 59051257HCID 59051257, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86643254HCID 86643254, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 11-oxo-11H-dibenzo[b,e][1,4]dioxepine-4-carboxylic acid (256 mg, 1 mmol) in methylene chloride (15 ml) was added BH3-dimethyl sulfide complex (1.6 ml, 1 mol/L in methylene chloride) under ice bath. The mixture was stirred for 30 min at room temperature, refluxed for 5 h and then cooled. The reaction was quenched by addition of methanol, and the whole mixture was evaporated by a rotatory evaporator. The residue was diluted with saturated NaHCO3 (aq) and extracted with AcOEt. The organic layer was washed with saturated brine, dried over anhydrous MgSO4, purified by column chromatography and evaporated by a rotatory evaporator. To a solution of the crude product in CH2Cl2 (20 ml) was added a suspension of pyridinium chlorochromate (PCC, 280 mg, 1.3 mmol) and neutral Al2O3 (350 mg) in CH2Cl2 (20 ml) in ice bath under N2. The mixture was stirred for 18 h at room temperature, filtered, evaporated by a rotatory evaporator, purified by column chromatography to obtain 11-oxo-11H-dibenzo[b,e][1,4]dioxepine-4-carbaldehyde.

Workup

  1. temperaturerefluxed for 5 h
  2. temperaturecooled
  3. customThe reaction was quenched by addition of methanol
  4. customthe whole mixture was evaporated by a rotatory evaporator
  5. additionThe residue was diluted with saturated NaHCO3 (aq)
  6. extractionextracted with AcOEt
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous MgSO4
  9. custompurified by column chromatography
  10. customevaporated by a rotatory evaporator
  11. additionTo a solution of the crude product in CH2Cl2 (20 ml) was added
  12. stirringThe mixture was stirred for 18 h at room temperature
  13. filtrationfiltered
  14. customevaporated by a rotatory evaporator
  15. custompurified by column chromatography

Sources & evidence

ORD record
ord-74d4af47bd214bba9f1256f74c4f854f
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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