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

HRID 1992941Notes

Reaction equation

HRID 1992941 reaction equation
[CH2:1]([C:5]1[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[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:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[CH2:1]([C:5]1[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]([O:15][C:23]2[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=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 685362243-Butyl-2-phenyl-1-naphthalenol

Product 1

HCID 860871264-[(3-Butyl-2-phenyl-1-naphthalenyl)oxy]benzaldehydeYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Butyl-2-phenyl-1-naphthalenol (172) (0.30 g, 1.09 mmol) and 4-fluorobenzaldehyde was heated with Cs2CO3 in DMSO at 100° C. to give 0.28 g (67%) of the title compound (173) as a light yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.77 (t, J=7.3 Hz, 3H), 1.15-1.30 (m, 2H), 1.40-1.55 (m, 2H), 2.58 (t, J=7.8 Hz, 2H), 6.68 (d, J=8.6 Hz, 2H), 7.08-7.14 (m, 2H), 7.19-7.26 (m, 3H), 7.39 (t, J=7.4 Hz, 1H), 7.50 (1, J=7.3 Hz, 1H), 7.62 (d, J=8.8 Hz, 2H), 7.71 (s, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.88 (d, J=8.3 Hz, 1H), 9.79 (s, 1H). LCMS (APCI): m/z 381 (M+H)+.

Sources & evidence

ORD record
ord-4003adb7805449c08206685b26591cab
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…