Sodium hydride → HCID 86616656, compound

HRID 1992905Notes

Reaction equation

HRID 1992905 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][C:22]([F:25])([F:24])[F:23])=[CH:6]2.[H-].[Na+].F[C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[O:34])=[CH:31][CH:30]=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:29]1[CH:36]=[CH:35][C:32]([CH:33]=[O:34])=[CH:31][CH:30]=1)=[C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([CH2:20][CH2:21][C:22]([F:24])([F:23])[F:25])=[CH:6]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 68536661HCID 68536661, compound

Product 1

HCID 86616656HCID 86616656, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(Methyloxy)-2-phenyl-3-(3,3,3-trifluoropropyl)-1-naphthalenol (125) (0.35 g, 1.00 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.32 g (71%) of the title compound (126) as a light yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 2.10-2.25 (m, 2H), 2.80-2.90 (m, 2H), 3.94 (s, 3H), 6.67 (d, J=8.8 Hz, 2H), 7.07-7.14 (m, 3H), 7.18 (d, J=2.4 Hz, 1H), 7.22-7.30 (m, 3H), 7.60-7.64 (m, 3H), 7.70 (d, J=9.2 Hz, 1H), 9.80 (s, 1H). LCMS (ESI): m/z 451 (M+H)+.

Sources & evidence

ORD record
ord-250958e87c19474bab61ca1d7e5bfa6a
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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