Sodium hydride → HCID 86616648, compound

HRID 1992867Notes

Reaction equation

HRID 1992867 reaction equation
[CH3:1][CH:2]([C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([OH:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:3].[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>[CH3:3][CH:2]([C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([O:16][C:26]2[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:1]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 68537270HCID 68537270, compound

Product 1

HCID 86616648HCID 86616648, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1-Methylethyl)-6-(methyloxy)-2-phenyl-1-naphthalenol (72) (0.35 g, 1.21 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.44 g (91%) of the title compound (73) as a light yellow foam. 1H NMR (400 MHz, CDCl3): δ 1.20 (d, J=6.8 Hz, 6H), 2.91 (sept, J=6.8 Hz, 1H), 3.94 (s, 3H), 6.67 (d, J=8.8 Hz, 2H), 7.05 (dd, J1=9.0 Hz, J2=2.4 Hz, 1H), 7.08-7.13 (m, 2H), 7.18-7.26 (m, 4H), 7.61 (d, J=8.6 Hz, 2H), 7.64-7.70 (m, 2H), 9.79 (s, 1H). LCMS (ESI): m/z 397 (M+H)+.

Sources & evidence

ORD record
ord-347d9de34dd34da0b897b3661899242a
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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