Ethyl Acetate → HCID 10721431, compound

HRID 482360Notes

Reaction equation

HRID 482360 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.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

4

Reactant 2

HCID 8857Ethyl AcetateHCID 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-dicyclo-hexylcarbodiimnide (515 mg, 2.5 mmol) was added aqueous IM 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-a0398d4455664fd7948bd3a035f47f6b
Source dataset
uspto-grants-1998_08
Patent number
US05795900

Reaction notes

Loading…