Cesium carbonate → 4-({3-Butyl-2-[4-(methyloxy)phenyl]-1-naphthalenyl}oxy)benzaldehyde

HRID 1992932Notes

Reaction equation

HRID 1992932 reaction equation
[CH2:1]([C:5]1[C:6]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:7]([OH:15])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4].F[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[CH2:1]([C:5]1[C:6]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[C:7]([O:15][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 685374103-Butyl-2-[4-(methyloxy)phenyl]-1-naphthalenol

Product 1

HCID 860871154-({3-Butyl-2-[4-(methyloxy)phenyl]-1-naphthalenyl}oxy)benzaldehydeYield 69%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Butyl-2-[4-(methyloxy)phenyl]-1-naphthalenol (160) (0.25 g, 0.82 mmol) and 4-fluorobenzaldehyde was heated with Cs2CO3 in DMSO at 100° C. to give 0.23 g (69%) of compound 161 as a light brown viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.80 (t, J=7.3 Hz, 3H), 1.20-1.30 (m, 2H), 1.40-1.50 (m, 2H), 2.60 (t, J=7.8 Hz, 2H), 3.78 (s, 3H), 6.71 (d, J=8.8 Hz, 2H), 6.79 (d, J=8.6 Hz, 2H), 7.05 (d, J=8.7 Hz, 2H), 7.39 (t, J=7.4 Hz, 1H), 7.50 (t, J=7.5 Hz, 1H), 7.64 (d, J=8.8 Hz, 2H), 7.70 (s, 1H), 7.77 (d, J=8.2 Hz, 1H), 7.87 (d, J=8.1 Hz, 1H), 9.81 (s, 1H). LCMS (ESI): m/z 411 (M+H)+.

Sources & evidence

ORD record
ord-cf59c30338ff48c3bbc0dedded3492cb
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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