Boron trifluoride etherate → HCID 58712184, compound

HRID 1528508Notes

Reaction equation

HRID 1528508 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-f8fa8a98d141406f88360573e5d5dfc0
Source dataset
uspto-grants-2015_07
Patent number
US09090603B2

Reaction notes

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