Boron Trichloride → HCID 19594704, compound

HRID 612611Notes

Reaction equation

HRID 612611 reaction equation
C([O:4][C:5]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:6]=1[C:7]1[C:8]([O:23][CH3:24])=[CH:9][C:10]([O:19][CH2:20][CH2:21][CH3:22])=[CH:11][C:12]=1[C:13]2=[O:18])(C)C.B(Cl)(Cl)Cl>C(Cl)Cl>[OH:4][C:5]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:6]=1[C:7]1[C:8]([O:23][CH3:24])=[CH:9][C:10]([O:19][CH2:20][CH2:21][CH3:22])=[CH:11][C:12]=1[C:13]2=[O:18]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 11141969HCID 11141969, compound

Product 1

HCID 19594704HCID 19594704, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepare a stirred solution of 5-isopropoxy-2-propoxy-4-methoxy-fluoren-9-one (2.2 g, 6.7 mmole) in 100 mL methylene chloride at 0° under argon. Dropwise add boron trichloride (15.4 mL of 1.0 M in methylene chloride, 15.4 mmole). Monitor the reaction by TLC on aliquots, in 40% ethyl acetate/hexane, quenching with saturated ammonium chloride. After 1 hour, quench the reaction with saturated ammonium chloride. Filter and wash twice with 1.00 mL methylene chloride. Separate the organic layer from the filtrate and wash with brine. Dry with magnesium sulfate, filter and strip the solvent. Chromatograph the crude product dissolving first in methylene chloride, then eluting in 30% ethyl acetate/hexane to give the title compound as a red powder (1.75 g, 6.1 mmole, 92%). Rf =0.54 (EtOAc/hex., 40:60).

Workup

  1. customMonitor the reaction by TLC on aliquots
  2. customin 40% ethyl acetate/hexane, quenching with saturated ammonium chloride
  3. customquench
  4. customthe reaction with saturated ammonium chloride
  5. filtrationFilter
  6. washwash twice with 1.00 mL methylene chloride
  7. customSeparate the organic layer from the filtrate
  8. washwash with brine
  9. dry with materialDry with magnesium sulfate
  10. filtrationfilter
  11. dissolutionChromatograph the crude product dissolving first in methylene chloride
  12. washeluting in 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b9d61e8f846f4cd38b9481c9a9ccd78a
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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