Tetrahydrofuran → 1-(2-Methoxyphenyl)naphthalene

HRID 1510181Notes

Reaction equation

HRID 1510181 reaction equation
C1COCC1.[C:6]1([Mg]Br)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.Cl[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26].[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C>CCCCCC.C1(C)C=CC=CC=1>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 130112-ChloroanisoleHCID 184547821,3-BIS(2,6-DIISOPROPYLPHENYL)imidazoLIDINIUM-CHLORIDEHCID 178418298HCID 178418298, compound

Product 1

HCID 543851171-(2-Methoxyphenyl)naphthaleneYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

Using a THF solution of 1-naphthylmagnesium bromide (4.62 mL, 0.26 M, 1.2 mmol), 1-chloro-2-methoxybenzene (142.6 mg, 1.0 mmol), FeF3.3H2O (8.34 mg, 0.05 mmol) and 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (64.1 mg, 0.15 mmol) as starting materials, the reaction was performed at a scale of 1.0 mmol at 70° C. for 48 hours in the same manner as in Example 2. After performing silica gel column chromatography (toluene=10, 20 and 40% in hexane), the above compound was obtained as a white solid (0.215 g, yield=92%, purity=>99% (GC analysis)).

Workup

  1. customthe above compound was obtained as a white solid (0.215 g, yield=92%, purity=>99% (GC analysis))

Sources & evidence

ORD record
ord-cc9899b0008d4c3abeab8346d99d8a71
Source dataset
uspto-grants-2012_07
Patent number
US08211820B2

Reaction notes

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