Sodium hydride → HCID 86087174, compound

HRID 1992959Notes

Reaction equation

HRID 1992959 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][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:6]2.[H-].[Na+].F[C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=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:31]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1)=[C:8]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:7]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:6]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 68541212HCID 68541212, compound

Product 1

HCID 86087174HCID 86087174, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(Methyloxy)-3-octyl-2-phenyl-1-naphthalenol (193) (0.60 g, 1.66 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.72 g (93%) of the title compound (194) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.84 (t, J=7.0 Hz, 3H), 1.05-1.30 (m, 10H), 1.40-1.50 (m, 2H), 2.54 (t, J=7.9 Hz, 2H), 3.94 (s, 3H), 6.67 (d, J=8.4 Hz, 2H), 7.03-7.14 (m, 3H), 7.16-7.26 (m, 4H), 7.56-7.64 (m, 3H), 7.67 (d, J=9.1 Hz, 1H), 9.79 (s, 1H). LCMS (APCI): m/z 467 (M+H)+.

Sources & evidence

ORD record
ord-9ff4e25050564a39890a82c92bb0231f
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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