Sodium hydride → HCID 86087180, compound

HRID 1992884Notes

Reaction equation

HRID 1992884 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][CH2:21][CH3:22])=[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][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1)=[C:8]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:7]([CH2:20][CH2:21][CH3:22])=[CH:6]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 68538683HCID 68538683, compound

Product 1

HCID 86087180HCID 86087180, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(Methyloxy)-2-phenyl-3-propyl-1-naphthalenol (97) (0.54 g, 1.86 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.66 g (89%) of the title compound (98) as a light yellow foam. 1H NMR (400 MHz, CDCl3): δ 0.81 (t, J=7.3 Hz, 3H), 1.40-1.55 (m, 2H), 2.53 (t, J=7.7 Hz, 2H), 3.94 (s, 3H), 6.67 (d, J=8.7 Hz, 2H), 7.05 (dd, J1=9.0 Hz, J2=2.5 Hz, 1H), 7.08-7.14 (m, 2H), 7.18 (d, J=2.5 Hz, 1H), 7.19-7.25 (m, 3H), 7.58-7.64 (m, 3H), 7.67 (d, J=9.2 Hz, 1H), 9.79 (s, 1H). LCMS (ESI): m/z 397 (M+H)+.

Sources & evidence

ORD record
ord-85d8688f88fe4f3a854972945a75d896
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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