Cesium carbonate → HCID 14349146, compound

HRID 414855Notes

Reaction equation

HRID 414855 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[O:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:27]1[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=1)[OH:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.[I-].[Na+].CCOCC>[O:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=1)[O:33][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[OH:26])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 14349171HCID 14349171, compound

Product 1

HCID 14349146HCID 14349146, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-chloromethyl quinoline (1.1 g; 6.3 mmol), 3-(6-phenoxy-1-hydroxyhexyl)phenol (1.8 g, 6.3 mmol) and finely powdered anhydrous potassium carbonate (1.74 g, 12.6 mmol) in acetone (40 ml) containing catalytic amounts of finely powdered, anhydrous cesium carbonate (0.4, 1.3 mmol) and sodium iodide (0.05 g, 0.33 mmol) was refluxed overnight (15 hours). The reaction mixture was cooled to the room temperature and filtered. The solid residue was washed thrroughly with acetone (3×15 ml), and all the filtrates were combined. All volatiles were removed from the combined acetone filtrate to leave a light yellow viscous liquid which solidifed to an off-white solid on trituration with a 1:1 mixture of ether and petroleum ether (35°-55° C.). This solid was chromatographed on silica gel with 35% ethylacetate in hexanes to yield the desired product (1.6 g, 60%) as a white crystalline solid, mp 83°-84.5° C.

Workup

  1. temperaturewas refluxed overnight (15 hours)
  2. filtrationfiltered
  3. washThe solid residue was washed thrroughly with acetone (3×15 ml), and all the filtrates
  4. customAll volatiles were removed from the combined acetone filtrate
  5. customto leave a light yellow viscous liquid which
  6. customThis solid was chromatographed on silica gel with 35% ethylacetate in hexanes

Sources & evidence

ORD record
ord-7cc47fc8aef54584a07c15bfe90779f5
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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