Dimethylformamide → HCID 18399658, compound

HRID 1018949Notes

Reaction equation

HRID 1018949 reaction equation
CN(C)[CH:3]=[O:4].P(Br)(Br)[Br:7].[CH2:10]1[O:22][C:21]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C:17](=O)[CH2:18]3)=[CH:13][C:12]=2[O:11]1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Br:7][C:17]1[CH2:16][CH2:15][C:14]2[C:19](=[CH:20][C:21]3[O:22][CH2:10][O:11][C:12]=3[CH:13]=2)[C:18]=1[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 12843073HCID 12843073, compound

Product 1

HCID 18399658HCID 18399658, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

Dimethylformamide (0.8 ml, 10 mmol) was added dropwise to a solution of phosphorus tribromide (0.8 ml, 8.5 mmol) in dry chloroform (20 ml) at 0° C. The mixture was stirred at 0° C. for 1 h to give pale yellow suspension. A solution of compound 6,7-methylenedioxy-2-tetralone (500 mg, 2.6 mmol) in dry chloroform(20 ml) was added to the yellow suspension and the mixture was heated at reflux for 1 h. The reaction mixture was cooled to 0° C. and saturated aqueous NaHCO3 solution was added dropwise until no effervescence was obtained. The resulting mixture was extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was chromatographed over 100 g of silica gel using 3:1 mixture respectively of hexanes and ethyl acetate to give the aldehyde in 60% yield; 1H NMR(CDCl3) δ2.80(2H, t, J=7.8), 2.98(2H, t, J=7.8), 5.93(2H, s), 6.64(1H, s), 7.57(1H, s), 10.28(1H, s); 13C NMR(CDCl3) δ29.3, 30.4, 101.6, 107.3,108.6, 124.0, 129.7, 132.7, 114.0, 146.7, 147.7, 193.2.

Workup

  1. customto give pale yellow suspension
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 1 h
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. customwas obtained
  6. extractionThe resulting mixture was extracted with dichloromethane
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was chromatographed over 100 g of silica gel using 3:1 mixture respectively of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-4e982e378e10493d9f633704a32ea99c
Source dataset
uspto-grants-2002_11
Patent number
US06486167B1

Reaction notes

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