Cesium carbonate → HCID 21957483, compound

HRID 2213570Notes

Reaction equation

HRID 2213570 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:11]=[O:12].[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31]Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:11]=[O:12]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 23393Picolyl chlorideHCID 219574673-Hydroxy-4-(2-phenylethoxy)benzaldehyde

Product 1

HCID 21957483HCID 21957483, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (800 mg, 2.5 mmol, 2 eq) was added to a stirred solution of 3-hydroxy-4-(2-phenylethoxy)-benzaldehyde (300 mg, 1.24 mmol, 1 eq), 2-picolyl chloride (210 mg, 1.3 mmol, 1.05 eq) and tetra-n-butylammonium iodide (460 mg, 1.24 mmol, 1 eq) in N,N-dimethylformamide (10 mL). The solution was stirred overnight, then concentrated in vacuo. The residue was azeotroped with water (2×10 mL), toluene (2×10 mL) and then purified by chromatography on silica gel. Elution with petroleum ether:ethyl acetate (1:1) gave the product as a white powder (367 mg, 89%). 1H NMR (CDCl3) δ 9.75 (s, 1H, O═C—H), 8.55 (d, 1H, J 4.9 Hz, pyH), 7.66 (ddd, 1H, J 7.5, 7.5 and 1.9 Hz, PyH), 7.47 (d, 1H, J 7.5 Hz, ArH), 5.22 (s, 2H, OCH2Py), 4.27 (t, 2H, J 7.2 Hz, OCH2CH2Ph), 3.15 (t, 2H, J 7.2 Hz, OCH2CH2Ph).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was azeotroped with water (2×10 mL), toluene (2×10 mL)
  3. custompurified by chromatography on silica gel
  4. washElution with petroleum ether:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-ae8a6304ddb34c2fbfc2de1ea414e369
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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