Dimethylformamide → 2-Butyl-1-benzofuran-3-carbaldehyde

HRID 735882

Reaction equation

HRID 735882 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)(Cl)=O.[CH2:11]([C:15]1[O:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[CH:19]=1)[CH2:12][CH2:13][CH3:14]>C(Cl)Cl>[CH2:11]([C:15]1[O:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[C:19]=1[CH:4]=[O:5])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 779512-Butylbenzofuran

Product 1

HCID 49619662-Butyl-1-benzofuran-3-carbaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DMF (59 g, 0.805 mol) in anhydrous DCM (300 mL) was added slowly at 0° C. under N2 atmosphere phosphorous oxy-chloride (123 g, 0.84 mol). The mixture was stirred at rt for 2 h. To this was added slowly 2-butyl-1-benzofuran (35 g, 0.21 mol) in anhydrous DCM (100 mL). The reaction mixture was slowly heated to 60° C. for 72 h, cooled to rt and poured into ice and extracted with EtOAc. The organic layer was washed with water, brine and dried over MgSO4. The solvent was removed under vacuum and the crude product purified by column chromatography over silica gel (PetEther/EtOAc) to give 2-butyl-1-benzofuran-3-carbaldehyde (30 g, 74%) as a light brown liquid.

Workup

  1. temperatureThe reaction mixture was slowly heated to 60° C. for 72 h
  2. temperaturecooled to rt
  3. additionpoured into ice
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under vacuum
  8. customthe crude product purified by column chromatography over silica gel (PetEther/EtOAc)

Sources & evidence

ORD record
ord-16efdabdfbd749c3a27507951c718c6a
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Linked notes

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