Cesium carbonate → 4-{[6-(Methyloxy)-3-pentyl-2-phenyl-1-naphthalenyl]oxy}benzaldehyde

HRID 1992898Notes

Reaction equation

HRID 1992898 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]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:6]2.F[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=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:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1)=[C:8]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:7]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:6]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 685347346-(Methyloxy)-3-pentyl-2-phenyl-1-naphthalenol

Product 1

HCID 860870414-{[6-(Methyloxy)-3-pentyl-2-phenyl-1-naphthalenyl]oxy}benzaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(Methyloxy)-3-pentyl-2-phenyl-1-naphthalenol (113) (0.41 g, 1.28 mmol) and 4-fluorobenzaldehyde was heated with Cs2CO3 in DMF at 100° C. to give 0.44 g (80%) of the title compound (114) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.78 (t, J=6.8 Hz, 3H), 1.10-1.25 (m, 4H), 1.40-1.55 (m, 2H), 2.47 (t, J=7.9 Hz, 2H), 3.94 (s, 3H), 6.68 (d, J=8.6 Hz, 2H), 7.05 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.08-7.14 (m, 2H), 7.18 (d, J=2.4 Hz, 1H), 7.19-7.25 (m, 3H), 7.58-7.64 (m, 3H), 7.67 (d, J=9.1 Hz, 1H), 9.79 (s, 1H). LCMS (ESI): m/z 425 (M+H)+.

Sources & evidence

ORD record
ord-1d2f9502deca414b9596f2aa1453c2ce
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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