Sodium hydride → 4-{[3-Butyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}benzaldehyde

HRID 1992874Notes

Reaction equation

HRID 1992874 reaction equation
[CH2:1]([C:5]1[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]([OH:17])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].F[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1>CN(C=O)C>[CH2:1]([C:5]1[C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]([O:17][C:27]2[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 685373173-Butyl-6-(methyloxy)-2-phenyl-1-naphthalenol

Product 1

HCID 860871424-{[3-Butyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}benzaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Butyl-6-(methyloxy)-2-phenyl-1-naphthalenol (81) (0.25 g, 0.82 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.27 g (82%) of 82 as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.77 (t, J=7.3 Hz, 3H), 1.10-1.25 (m, 2H), 1.40-1.50 (m, 2H), 2.55-2.60 (m, 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), 7.08-7.13 (m, 2H), 7.17 (d, J=2.6 Hz, 1H), 7.18-7.25 (m, 3H), 7.58-7.64 (m, 3H), 7.67 (d, J=9.1 Hz, 1H), 9.79 (s, 1H). LCMS (ESI): m/z 411 (M+H)+.

Sources & evidence

ORD record
ord-5fcea0073b0243e6a2b1e5d3cc93424a
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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