Sodium hydride → 4-[(3-Methyl-2-phenyl-1-naphthalenyl)oxy]benzaldehyde

HRID 1992877Notes

Reaction equation

HRID 1992877 reaction equation
[CH3:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([OH:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Na+].F[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1>CN(C=O)C>[CH3:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([O:12][C:22]2[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 685367573-Methyl-2-phenyl-1-naphthalenol

Product 1

HCID 860871604-[(3-Methyl-2-phenyl-1-naphthalenyl)oxy]benzaldehydeYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-2-phenyl-1-naphthalenol (86) (0.11 g, 0.48 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.12 g (70%) of the title compound (87) as a colorless viscous oil. 1H NMR (400 MHz, CDCl3): δ 2.27 (s, 3H), 6.71 (d, J=8.8 Hz, 2H), 7.10-7.16 (m, 2H), 7.20-7.30 (m, 3H), 7.39 (t, J=7.4 Hz, 1H), 7.50 (t, J=7.2 Hz, 1H), 7.62 (d, J=8.6 Hz, 2H), 7.71 (s, 1H), 7.78 (d, J=8.2 Hz, 1H), 7.85 (d, J=8.2 Hz, 1H), 9.80 (s, 1H). LCMS (ESI): m/z 339 (M+H)+.

Sources & evidence

ORD record
ord-580edb5f1daa433a83b6ae5916bcb00e
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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