Water → HCID 10722005, compound

HRID 482364Notes

Reaction equation

HRID 482364 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([CH3:21])([CH3:20])[CH:5]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]([CH3:20])([CH3:21])[CH:5]([C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:30][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=2)=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:30][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 203942-(Chloromethyl)quinolineHCID 10661943HCID 10661943, compound

Product 1

HCID 10722005HCID 10722005, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution in DMF (50 mL) of 2,2-dimethyl-3,3-bis(4-hydroxy-phenyl)propionic acid methyl ester (1.1 g, 3.7 mmol), prepared as in step 1, was added Cs2CO3 (2.5 g, 7.7 mmol) and the mixture stirred 0.5 hours at room temperature. 2-Chloromethyquinoline (1.37g, 7.7 mmol) was added as a solid in small portions. The reaction mixture was stirred overnight at room temperature. The mixture was poured into 300 mnL of water and extracted with ether (2×200 mL). Brine was added to the aqueous layer and it was extracted twice with ether. The combined ether extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give a light yellow oil. Chromatography on silica gel (40% ethyl acetate/hexanes) gave 1.68 g (78%) of 2,2-dimethyl-3,3-bis(4-(2-quinolyl-methoxy)phenyl)propionic acid methyl ester as a white foam.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. extractionextracted with ether (2×200 mL)
  3. additionBrine was added to the aqueous layer and it
  4. extractionwas extracted twice with ether
  5. washThe combined ether extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a light yellow oil

Sources & evidence

ORD record
ord-21622c88040d4c7dbfe3e64f2e229333
Source dataset
uspto-grants-1998_08
Patent number
US05795900

Reaction notes

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