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

HRID 1992891Notes

Reaction equation

HRID 1992891 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][CH:21]([CH3:23])[CH3:22])=[CH:6]2.[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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1)=[C:8]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:7]([CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:6]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 685409276-(Methyloxy)-3-(2-methylpropyl)-2-phenyl-1-naphthalenol

Product 1

HCID 866166534-{[6-(Methyloxy)-3-(2-methylpropyl)-2-phenyl-1-naphthalenyl]oxy}benzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(Methyloxy)-3-(2-methylpropyl)-2-phenyl-1-naphthalenol (105) (0.66 g, 2.16 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.74 g (83%) of the title compound (106) as a light yellow foam. 1H NMR (400 MHz, CDCl3): δ 0.75 (d, J=6.8 Hz, 6H), 1.60-1.70 (m, 1H), 2.47 (d, J=7.1 Hz, 2H), 3.94 (s, 3H), 6.67 (d, J=8.8 Hz, 2H), 7.05 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.07-7.12 (m, 2H), 7.15-7.25 (m, 4H), 7.56 (s, 1H), 7.61 (d, J=8.6 Hz, 2H), 7.67 (d, J=9.1 Hz, 1H), 9.79 (s, 1H). LCMS (ESI): m/z 411 (M+H)+.

Sources & evidence

ORD record
ord-4f019d86a635496e93d57d84ac9f3fe7
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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