Ammonia → Methyl 4-ethoxycarbonyl-3-oxopentanoate

HRID 654998Notes

Reaction equation

HRID 654998 reaction equation
[O:1]=[C:2]([CH:10]([C:14]([O:16][CH3:17])=[O:15])C(=O)C)[CH:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].N>O1CCCC1>[CH2:7]([O:6][C:4]([CH:3]([CH3:9])[C:2](=[O:1])[CH2:10][C:14]([O:16][CH3:17])=[O:15])=[O:5])[CH3:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14348548Ethyl 3,5-dioxo-4-methoxycarbonyl-2-methylhexanoate

Product 1

HCID 14348549Methyl 4-ethoxycarbonyl-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3,5-dioxo-4-methoxycarbonyl-2-methylhexanoate (176 mg; 0.72 mmole) was dissolved in tetrahydrofuran (1.3 ml), and 1.7N aqueous ammonia (0.85 ml) was added thereto at room temperature. The resultant mixture was allowed to stand at the same temperature overnight, followed by removal of tetrahydrofuran under reduced pressure. The reaction mixture was combined with lN hydrochloric acid (0.7 ml) and an aqueous sodium chloride solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give methyl 4-ethoxycarbonyl-3-oxopentanoate.

Workup

  1. customat room temperature
  2. customto stand at the same temperature overnight
  3. customfollowed by removal of tetrahydrofuran under reduced pressure
  4. extractionan aqueous sodium chloride solution and extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff3b43f7b9cc4362acc0fed0dd6022c9
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

Loading…