Cesium carbonate → HCID 86616674, compound

HRID 1992992Notes

Reaction equation

HRID 1992992 reaction equation
CC(N(C)C)=O.[CH3:7][C:8]1[C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)=[C:10]([OH:20])[C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2.F[C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:7][C:8]1[C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)=[C:10]([O:20][C:30]2[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=2)[C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 680234-FluorobenzaldehydeHCID 68534677HCID 68534677, compound

Product 1

HCID 86616674HCID 86616674, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dimethylacetamide solution (2 mL) of 3-methyl-6-(methyloxy)-2-[3-(methyloxy)phenyl]-1-naphthalenol (247) (0.072 g, 0.25 mmol, 1 equiv) was treated with 4-fluorobenzaldehyde (0.030 mL, 0.27 mmol, 1.1 equiv) followed by cesium carbonate (0.096 g, 0.29 mmol, 1.2 equiv). After 10 min at gentle reflux, the mixture was diluted with H2O (2 mL) and extracted with EtOAc (3×5 mL). The pooled organic portions were dried (Na2SO4) and concentrated. Radial chromatography (SiO2, 1 mm plate, 80:20; hexanes/EtOAc) afforded the title compound (248) as a pale yellow oil (0.060 g, 61%). 1H NMR (CDCl3, 300 MHz) δ 9.80 (s, 1H), 7.68-7.59 (m, 4H), 7.19-7.14 (m, 2H), 7.05 (dd, J=9.2, 2.4 Hz, 1H), 6.78-6.65 (m, 5H), 3.93 (s, 3H), 3.64 (s, 3H), 2.26 (s, 3H). TLC (75:25; hexanes/EtOAc): Rf=0.55.

Workup

  1. extractionextracted with EtOAc (3×5 mL)
  2. dry with materialThe pooled organic portions were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-16ac9ac019894f2b903b5414bedd9f29
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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