2,4,6-Tris((dimethylamino)methyl)phenol → Ethyl 7-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-chromane-2-carboxylate

HRID 479632Notes

Reaction equation

HRID 479632 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1.[C:17]1([O:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33]Br)=[C:26]([CH2:35][CH2:36][CH3:37])[CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>>[CH2:35]([C:26]1[CH:25]=[C:24]([O:23][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH2:31][CH2:32][CH2:33][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1)[CH2:36][CH3:37]

Participants

5

Reactant 4

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 10796Cesium carbonateHCID 11085381Ethyl 7-hydroxychromane-2-carboxylateHCID 187722731-(3-bromopropoxy)-4-phenoxy-2-propylBenzene

Product 1

HCID 18772266Ethyl 7-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-chromane-2-carboxylateYield 76%

Conditions

Temperature
70 °C

Procedure

To a 50 ml round-bottom flask were added ethyl 7-hydroxychromane-2-carboxylate (100 mg, 0.45 mmol), 4-(3-bromopropoxy)-3-propylphenyl phenyl ether (U.S. Pat. No. 6,008,237) (188 mg, 0.54 mmol), cesium carbonate (176 mg, 0.54 mmol), and DMF 3 ml. The resulting suspension was stirred at 70° C. for 5 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and water. The organic layer was separated. The aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Eluting with 10% AcOEt/hexanes gave the title compound as a pale yellow oil 167 mg (76%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and water
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel
  9. washEluting with 10% AcOEt/hexanes

Sources & evidence

ORD record
ord-de6e3a706af54bc49ab9fde730dd9b1b
Source dataset
uspto-grants-2003_11
Patent number
US06645997B2

Reaction notes

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