Sodium hydride → HCID 86616644, compound

HRID 1992844Notes

Reaction equation

HRID 1992844 reaction equation
[CH3:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:4]([OH:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.[H-].[Na+].F[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1>CN(C=O)C>[CH3:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:4]([O:14][C:26]2[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 68539548HCID 68539548, compound

Product 1

HCID 86616644HCID 86616644, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-6-(methyloxy)-2-[4-(methyloxy)phenyl]-1-naphthalenol (45) (0.30 g, 1.00 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.32 g (81%) of the title compound (46) as a light yellow foam. 1H NMR (400 MHz, CDCl3): δ 2.26 (s, 3H), 3.76 (s, 3H), 3.93 (s, 3H), 6.71 (d, J=8.8 Hz, 2H), 6.79 (d, J=8.7 Hz, 2H), 7.02-7.07 (m, 3H), 7.14 (d, J=2.6 Hz, 1H), 7.58 (s, 1H), 7.63 (d, J=8.8 Hz, 2H), 7.66 (d, J=9.1 Hz, 1H), 9.80 (s, 1H). LCMS (APCI): m/z 399 (M+H)+.

Sources & evidence

ORD record
ord-3ac3e1f8495e43329dbc6233179402f7
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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