Boron trifluoride etherate → HCID 9859355, compound

HRID 1471884Notes

Reaction equation

HRID 1471884 reaction equation
[C:1]1([C:7]([CH:9]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3]C=1.B(F)(F)F.C[CH2:23][O:24]CC>CCOCC>[O:10]=[C:9]([C:7]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:1]=1)[CH:11]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:23]=[O:24]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 92219Chalcone epoxide

Product 1

HCID 9859355HCID 9859355, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

Phenyl(3-phenyloxiran-2-yl)methanone (5.0 g, 22.3 mmol) was suspended in dry Et2O (40 mL) under an argon balloon. Boron trifluoride diethyl etherate (3.00 mL, 23.7 mmol) was added slowly via syringe. The reaction was refluxed at 50° C. for an hour, then cooled and extracted with 60 mL each of H2O and Et2O/EtOAc. The aqueous layer was extracted again with EtOAc (60 mL). The combined organic layer was dried and concentrated to give 3-oxo-2,3-diphenylpropanal.

Workup

  1. temperaturecooled
  2. extractionextracted with 60 mL each of H2O and Et2O/EtOAc
  3. extractionThe aqueous layer was extracted again with EtOAc (60 mL)
  4. customThe combined organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-67ddf23372ac42789303eb09e4734a00
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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