Boron trifluoride etherate → HCID 67034856, compound

HRID 1035853Notes

Reaction equation

HRID 1035853 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[OH:19])=[O:8].[CH3:20]COCC.B(F)(F)F.P(Cl)(Cl)(Cl)(Cl)Cl>CN(C=O)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:7](=[O:8])[C:9]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([O:15][CH3:16])[CH:14]=2)[O:19][CH:20]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 24819Phosphorus pentachlorideHCID 51347972HCID 51347972, compound

Product 1

HCID 67034856HCID 67034856, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

1st method: A solution A is prepared from 500 mg of the compound of the above Step, 6-bromo-1-(2-hydroxy-4,5-dimethoxyphenyl)-hexan-1-one (1.5 mmol), dissolved in 0.60 ml (4.5 mmol) of Et2O—BF3, and the solution is cooled to 10° C. 2.3 ml of DMF are then added. There is prepared, in addition, a solution B of 4 ml of DMF and there is added thereto in small portions at 10° C. 470 mg (2.25 mmol) of PCl5. Solution B is heated at 55° C. for 20 min, and is then introduced dropwise into solution A, referred to at the beginning, with a return to ambient temperature. The mixture turns orangey yellow and precipitates. 50 ml of 0.1N HCl are introduced and the mixture is extracted with AcOEt, the organic phases are washed with saturated NaCl solution, separated, dried over MgSO4, filtered and evaporated. The residue is subjected to flash chromatography over SiO2 with a gradient of pure heptane to heptane-AcOEt 70-30. The purified fractions crystallise after evaporation. 300 mg of 3-(4-bromobutyl)-6,7-dimethoxychromen-4-one are obtained in the form of crystals (yield=59%); TLC SiO2hept-AcOEt 50-50 Rf=0.4.

Workup

  1. customThere is prepared, in addition
  2. customat 10° C
  3. customreferred to at the beginning, with a return to ambient temperature
  4. customprecipitates
  5. addition50 ml of 0.1N HCl are introduced
  6. extractionthe mixture is extracted with AcOEt
  7. washthe organic phases are washed with saturated NaCl solution
  8. customseparated
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated
  12. customThe purified fractions crystallise
  13. customafter evaporation

Sources & evidence

ORD record
ord-fe1bfa534f85490eb6fbc561e0581178
Source dataset
uspto-grants-2013_10
Patent number
US08546402B2

Reaction notes

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