Cesium carbonate → 4-[(6-Methoxy-3-methyl-2-phenyl-1-naphthyl)oxy]benzaldehyde

HRID 1992814Notes

Reaction equation

HRID 1992814 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([CH3:20])=[CH:6]2.F[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1)=[C:8]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:7]([CH3:20])=[CH:6]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 685363886-Methoxy-3-methyl-2-phenyl-1-naphthol

Product 1

HCID 860871594-[(6-Methoxy-3-methyl-2-phenyl-1-naphthyl)oxy]benzaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round-bottomed flask was charged with 3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenol (7) (2.5 g, 9.5 mmol), 4-fluorobenzaldehyde (1.22 mL, 11.4 mmol), Cs2CO3 (4.04 g, 12.4 mmol), and anhydrous DMF (25 mL) under N2. The reaction mixture was refluxed for 3 h. Reaction mixture was cooled at room temperature and purified by SiO2 column chromatography using hexanes:EtOAc (19:1 to 4:1) as an eluent to afford 3.41 g (98%) of the title compound as a white foam. 1H NMR (400 MHz, CDCl3): δ 9.80 (s, 1H), 7.68 (d, J=9.2 Hz, 1H), 7.62 (d, J=8.4 Hz, 2H), 7.61 (d, J=5.2 Hz, 1H), 7.25 (d, J=7.6 Hz, 2H), 7.22 (d, J=5.2 Hz, 1H), 7.15 (d, J=2.4 Hz, 1H), 7.14 (d, J=1.6 Hz, 1H), 7.11 (s, 1H), 7.07 and 7.04 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.71 (d, J=8.8 Hz, 2H), 3.94 (s, 3H), 2.26 (s, 3H). LCMS (ESI) m/z, 368.92 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customReaction mixture
  3. custompurified by SiO2 column chromatography

Sources & evidence

ORD record
ord-8046928b6f4b42f1b850224be3f8aec9
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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