Ethyl Acetate → HCID 10721431, compound

HRID 1456859Notes

Reaction equation

HRID 1456859 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:42]=[CH:41][C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]=3)=[CH:27][CH:26]=2)([CH3:24])[CH2:20][CH2:21][CH2:22][OH:23])=[CH:15][CH:14]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(OCC)(=O)C>CS(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:42]=[CH:41][C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]=3)=[CH:27][CH:26]=2)([CH3:24])[CH2:20][CH2:21][CH:22]=[O:23])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 10769106HCID 10769106, compound

Product 1

HCID 10721431HCID 10721431, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution in DMSO (20 mL) of 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentan-1-ol (410 mg, 0.74 mmol), prepared as in Example 4, and 1,3-dicyclohexylcarbodiimide (515 mg, 2.5 mmol) was added aqueous 1M phosophoric acid (0.5 mL) and the resulting mixture was stirred at room temperature for 4 hours. Ethyl acetate (80 mL) was added and dicyclohexylurea was filtered off. The filtrate was washed with water and brine dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (methylene chloride-ethyl acetate 9:1) to afford 280 mg of 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentanal.

Workup

  1. filtrationdicyclohexylurea was filtered off
  2. washThe filtrate was washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (methylene chloride-ethyl acetate 9:1)

Sources & evidence

ORD record
ord-89b8d6a9bd49431aa39661fcc6bfbce0
Source dataset
uspto-grants-1998_12
Patent number
US05843968

Reaction notes

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