Boron trifluoride etherate → HCID 58712184, compound

HRID 1362910Notes

Reaction equation

HRID 1362910 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[OH:10])[CH3:2].[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[CH2:21][C:22]#N.B(F)(F)F.CC[O:30]CC>>[CH2:1]([C:3]1[C:4]([OH:10])=[CH:5][C:6]([OH:9])=[C:7]([C:22](=[O:30])[CH2:21][C:12]2[CH:13]=[CH:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=2)[CH:8]=1)[CH3:2]

Participants

4

Reactant 3

HCID 8000Boron trifluoride etherateHCID 179274-EthylresorcinolHCID 820082-Naphthylacetonitrile

Product 1

HCID 58712184HCID 58712184, compound

Procedure

To a mixture of 4-ethyl-benzene-1,3-diol (a, 10 mmol) and naphthalen-2-yl-acetonitrile (b, 10 mmol) in boron trifluoride etherate (20 mL) was bubbled gaseous HCl for 12 h. The solids that formed were collected by filtration and heated in 6N HCl (100 mL) and EtOH (20 mL) for 6 h. The mixture was diluted with water and extracted with CH2Cl2. The organic extract was washed with water and dried. The oil obtained on concentration of the organic layer was crystallized in EtOAc/hexanes to give 1-(5-ethyl-2,4-dihydroxy-phenyl)-2-naphthalen-2-yl-ethanone (c, 0.74 g).

Workup

  1. customwas bubbled gaseous HCl for 12 h
  2. customThe solids that formed
  3. filtrationwere collected by filtration
  4. temperatureheated in 6N HCl (100 mL)
  5. additionThe mixture was diluted with water
  6. extractionextracted with CH2Cl2
  7. extractionThe organic extract
  8. washwas washed with water
  9. customdried
  10. customThe oil obtained on concentration of the organic layer
  11. customwas crystallized in EtOAc/hexanes

Sources & evidence

ORD record
ord-7662ff0490844ec397f57c913032f7b5
Source dataset
uspto-grants-2011_02
Patent number
US07884094B2

Reaction notes

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