Boron trifluoride etherate → HCID 20262447, compound

HRID 464688Notes

Reaction equation

HRID 464688 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2(O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 202624453-(3-Methoxyphenyl)-3-hydroxyindan-1-one

Product 1

HCID 20262447HCID 20262447, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(3-methoxyphenyl)-3-hydroxyindan-1-one (2.3 g) in 25 ml methylene chloride was stirred at 0°, then treated sequentially with 1.6 ml triethylsilane and 3.3 ml of boron trifluoride etherate. The mixture was warmed to 25° and stirred for 16 hours, then diluted with water and extracted with additional methylene chloride. After drying (MgSO4) and concentration, the residue was chromatographed on silica gel to provide the title compound as a light yellow oil (0.5 g, 23%). NMR and IR spectra were consistent with the assigned structure.

Workup

  1. temperatureThe mixture was warmed to 25°
  2. extractionextracted with additional methylene chloride
  3. customAfter drying
  4. concentration(MgSO4) and concentration
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-5683300d83044d3199f629641aa417c1
Source dataset
uspto-grants-1985_10
Patent number
US04548946

Reaction notes

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