Dimethylformamide → Dibenzofuran-3-carbaldehyde

HRID 1666787Notes

Reaction equation

HRID 1666787 reaction equation
[C:1]([Li])(C)(C)[CH3:2].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].CN(C)[CH:14]=[O:15].[O:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH:8]1[C:7]2[C:1]3[CH:2]=[CH:18][CH:19]=[CH:20][C:21]=3[O:17][C:6]=2[CH:11]=[C:10]([CH:14]=[O:15])[CH:9]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8058HexaneHCID 178418306HCID 178418306, compound

Product 1

HCID 13474591Dibenzofuran-3-carbaldehyde

Conditions

Temperature
-78 °C

Procedure

Combine 3-bromodibenzofuraan (0.5 g, 2.0 mmol) and tetrahydrofuran (30 ml). Cool to about −78° C. Add a solution of t-butyllithium, 1.6 M solution in hexane (2.2 ml, 3.0 mmol), then warn to about 0° C. for 10 min. Cool to about −78° C. and add dimethylformamide (0.5 ml, 5.9 mmol). Warm to room temperature, quench with water, and extract with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 8:2 hexane:EtOAc to give the title compound.

Workup

  1. temperatureCool to about −78° C.
  2. temperatureWarm to room temperature
  3. customquench with water
  4. extractionextract with dichloromethane
  5. washwash sequentially with distilled water and brine
  6. dry with materialdry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto give a residue
  10. washChromatograph the residue eluting with 8:2 hexane

Sources & evidence

ORD record
ord-3bbe3de33bdd4779b641f14d408ac722
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

Loading…