Ethyl Acetate → HCID 19606368, compound

HRID 1603915Notes

Reaction equation

HRID 1603915 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=1)=[O:2].CC(C)([O-])C.[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OCC)(=O)C>CN(C)C=O>[C:27]1([CH2:26][CH2:25][CH2:24][CH2:23][N:5]2[C:6]3[C:11](=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=3)[C:3]([CH:1]=[O:2])=[CH:4]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2596681-Bromo-4-phenylbutaneHCID 19606277Methyl 3-formyl-1H-indole-5-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 19606368HCID 19606368, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-formylindole-5-carboxylate (2.234 g, 11.0 mmol) and potassium tert-butoxide (1.259 g, 11.2 mmol) in dry N,N-dimethylformamide (50 ml) was added with 1-bromo-4-phenylbutane (2.385 g, 11.2 mmol) and left under stirring at room temperature for 18 h. After that the solvent was evaporated off under reduced pressure, the resulting residue was partitioned between a NaCl saturated solution (50 ml) and chloroform (50 ml) and the aqueous phase was extracted with chloroform (3×50 ml). After drying and evaporating off the solvent under reduced pressure, a crude was obtained which was purified by chromatography through a silica gel column, eluting with n-hexane:ethyl acetate, 70:30, thereby obtaining 2.847 g of the title compound (87% yield).

Workup

  1. waitleft
  2. customAfter that the solvent was evaporated off under reduced pressure
  3. customthe resulting residue was partitioned between a NaCl saturated solution (50 ml) and chloroform (50 ml)
  4. extractionthe aqueous phase was extracted with chloroform (3×50 ml)
  5. customAfter drying
  6. customevaporating off the solvent under reduced pressure
  7. customa crude was obtained which
  8. customwas purified by chromatography through a silica gel column
  9. washeluting with n-hexane

Sources & evidence

ORD record
ord-85a20250ed5f4d189e8e94bbf8c48387
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

Loading…