Sodium hydride → HCID 86616661, compound

HRID 1992925Notes

Reaction equation

HRID 1992925 reaction equation
[CH:1]1([C:4]2[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:6]([OH:16])[C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=3)[CH2:3][CH2:2]1.[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>[CH:1]1([C:4]2[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:6]([O:16][C:26]3[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=3)[C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=3)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 68539304HCID 68539304, compound

Product 1

HCID 86616661HCID 86616661, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Cyclopropyl-6-(methyloxy)-2-phenyl-1-naphthalenol (152) (0.18 g, 0.62 mmol) was treated with NaH in DMF followed by addition of 4-fluorobenzaldehyde to give 0.21 g (86%) of the title compound (153) as a yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.75-0.85 (m, 4H), 1.60-1.70 (m, 1H), 3.92 (s, 3H), 6.70 (d, J=8.6 Hz, 2H), 7.03 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 7.14 (d, J=2.4 Hz, 1H), 7.18-7.28 (m, 6H), 7.62 (d, J=8.7 Hz, 2H), 7.66 (d, J=9.1 Hz, 1H), 9.79 (s, 1H). LCMS (ESI): m/z 395 (M+H)+.

Sources & evidence

ORD record
ord-3be37440e2fd4d51a38e90d9b2ff3310
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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