Diethyl Ether → 2-(3'-Benzyloxy-5-methoxybiphenyl-2-yl)-6-methoxynaphthalene

HRID 1950302Notes

Reaction equation

HRID 1950302 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]=2)=[C:7](N)[CH:8]=1.F[B-](F)(F)F.[H+].N(O[CH2:31][CH2:32][CH:33]([CH3:35])C)=O.[CH2:36]([O:38][CH2:39][CH3:40])[CH3:37]>O1CCCC1>[CH2:36]([O:38][C:39]1[CH:31]=[C:32]([C:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]=2)[CH:33]=[CH:35][CH:40]=1)[C:37]1[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8053Isoamyl NitriteHCID 28118Tetrafluoroboric acidHCID 230875115-Methoxy-2-(6-methoxynaphthalen-2-yl)phenylamine

Product 1

HCID 230871832-(3'-Benzyloxy-5-methoxybiphenyl-2-yl)-6-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

The title compound was synthesized by referring to Tetrahedron Lett., 1996, 37, 3857. To a solution of 5-methoxy-2-(6-methoxynaphthalen-2-yl)phenyl amine (340 mg) in tetrahydrofuran (8 ml) was added tetrafluoroboric acid (42% aqueous solution) (0.22 ml) under a nitrogen atmosphere, the solution was cooled at −40° C., isoamyl nitrite (2.4 ml) was then added dropwise thereto followed by stirring for 2 hours at −40° C. Diethyl ether (20 ml) was added thereto and the solid that was precipitated was filtered. A suspension of the resulting 5-methoxy-2-(6-methoxynaphthalen-2-yl)benzenediazonium tetrafluoroborate (320 mg), 3-benzyloxyphenylboronic acid (235 mg) and palladium(II) acetate (10 mg) in 1,4-dioxane (4 ml) was stirred overnight at room temperature under a nitrogen atmosphere. Water was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (181 mg).

Workup

  1. customThe title compound was synthesized
  2. customthe solid that was precipitated
  3. filtrationwas filtered
  4. additionA suspension of the resulting 5-methoxy-2-(6-methoxynaphthalen-2-yl)benzenediazonium tetrafluoroborate (320 mg), 3-benzyloxyphenylboronic acid (235 mg) and palladium(II) acetate (10 mg) in 1,4-dioxane (4 ml)
  5. stirringwas stirred overnight at room temperature under a nitrogen atmosphere
  6. additionWater was added
  7. stirringby stirring
  8. extractionthe solution was extracted with ethyl acetate
  9. washsequentially washed with water and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated in vacuo
  12. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-a8042ce783a942ab9c9098e7b1a7e581
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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