Diisopropyl Ether → HCID 19610387, compound

HRID 1602114Notes

Reaction equation

HRID 1602114 reaction equation
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1/[CH:12]=[CH:13]/[CH:14]=[C:15](\[O:20][CH3:21])/[C:16]([O:18]C)=[O:17].C(OC(C)C)(C)C>CO>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1/[CH:12]=[CH:13]/[CH:14]=[C:15](\[O:20][CH3:21])/[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 14797Potassium HydroxideHCID 86754764HCID 86754764, compound

Product 1

HCID 19610387HCID 19610387, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of KOH (0.26 g, 4.7 mmol) in methanol (13 ml), methyl (2Z,4E)-5-(2-indolyl)-2-methoxy-2,4-pentadienoate (0.3 g, 1.17 mmol) was added and the solution was heated at 50° C. for 1 hour under nitrogen. The solvent was removed under vacuum and the residue was dissolved in water (20 ml) and washed with isopropyl ether. The aqueous phase was adjusted to pH 5 with 10% HCl and then extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and the solvent removed under reduced pressure obtaining, after trituration with isopropyl ether, 0.15 g (52.7%) of the title compound as a solid, m.p.=189-190° C.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in water (20 ml)
  3. washwashed with isopropyl ether
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed under reduced pressure
  8. customobtaining

Sources & evidence

ORD record
ord-01b3ea1e5bee45518cb776db50537ffc
Source dataset
uspto-grants-1999_11
Patent number
US05981525

Reaction notes

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