Cesium carbonate → 4-(2-Furan-2-yl-6-methoxy-3-methyl-naphthalen-1-yloxy)-benzaldehyde

HRID 1992970Notes

Reaction equation

HRID 1992970 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][CH2:14]OC)=[C:8]([C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)[C:7]([CH3:22])=[CH:6]2.Cl.O1CCOCC1.FC1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:8]1[C:7]([CH3:22])=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]=1[O:13][C:14]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 204431481,4-Dioxane hydrochlorideHCID 685396222-(6-Methoxy-1-methoxymethoxy-3-methyl-naphthalen-2-yl)-furan

Product 1

HCID 860872024-(2-Furan-2-yl-6-methoxy-3-methyl-naphthalen-1-yloxy)-benzaldehydeYield 36.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(6-Methoxy-1-methoxymethoxy-3-methyl-naphthalen-2-yl)-furan (213) (0.54, 1.8 mmol), 4 N HCl/Dioxane (6 mL), 4-fluorobenzaldehyde (0.23 mL, 2.17 mmol), Cs2CO3 (1.47 g, 4.53 mmol) and DMSO (8 mL) were reacted as described above to give 0.236 g (36%) of the title compound (214) as oil. 1H NMR (400 MHz, d-CDCl3): δ 2.48 (s, 3H), 3.93 (s, 3H), 6.34 (s, 2H), 6.84 (d, J=8.6 Hz, 2H), 7.04 (dd, J1=2.4 Hz, J2=9.2 Hz, 1H), 7.11-7.12 (m, 1H), 7.39 (s, 1H), 7.57 (s, 1H), 7.69-7.73 (m, 3H), 9.84 (s, 1H).

Sources & evidence

ORD record
ord-ffc6241c51d74987b5abf941abbc0764
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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