Cesium carbonate → 4-[2-(4-Fluoro-phenyl)-6-methoxy-3-propyl-naphthalen-1-yloxy]-2-trifluoromethyl-benzaldehyde

HRID 1992979Notes

Reaction equation

HRID 1992979 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([CH2:18][CH2:19][CH3:20])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:21][CH3:22])[CH:14]=3)[C:9]=2[O:23][CH2:24]OC)=[CH:4][CH:3]=1.Cl.O1CCOCC1.FC1[CH:42]=[CH:41][C:38]([CH:39]=[O:40])=[C:37]([C:43]([F:46])([F:45])[F:44])[CH:36]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]([CH2:18][CH2:19][CH3:20])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:21][CH3:22])[CH:14]=3)[C:9]=2[O:23][C:24]2[CH:42]=[CH:41][C:38]([CH:39]=[O:40])=[C:37]([C:43]([F:44])([F:46])[F:45])[CH:36]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 5229404-Fluoro-2-(trifluoromethyl)benzaldehydeHCID 204431481,4-Dioxane hydrochlorideHCID 685346522-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-propyl-naphthalene

Product 1

HCID 866166694-[2-(4-Fluoro-phenyl)-6-methoxy-3-propyl-naphthalen-1-yloxy]-2-trifluoromethyl-benzaldehydeYield 98.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-propyl-naphthalene (225) (0.6 g, 1.69 mmol), 4 N HCl/Dioxane (12 mL), 4-fluoro-2-trifluoromethyl-benzaldehyde (0.277 mL, 2.03 mmol), Cs2CO3 (1.38 g, 4.23 mmol) and DMSO (12 mL) were reacted as described above to give 0.80 g (98%) of the title compound (226) as oil. 1H NMR (400 MHz, d-CDCl3): δ 0.83 (t, J=7.3 Hz, 3H), 1.47-1.55 (m, 2H), 2.54 (t, J=7.8 Hz, 2H), 3.95 (s, 3H), 6.75 (dd, J=2.3, 8.7 Hz, 1H), 6.94-6.99 (m, 3H), 7.06-7.10 (m, 3H), 7.19 (m, 1H), 7.63-7.66 (m, 2H), 7.89 (d, J=8.8 Hz, 1H), 10.18-10.19 (m, 1H).

Sources & evidence

ORD record
ord-86a14962cc8140ea83a23dd3b88acaf6
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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