HCID 22257821, compound → HCID 22257788, compound

HRID 324575Notes

Reaction equation

HRID 324575 reaction equation
[O:1]=[C:2]([N:7]1[CH2:11][CH2:10][CH2:9][CH:8]1[C:12](=[O:17])[CH2:13][CH2:14][CH:15]=[CH2:16])[C:3]([O:5]C)=O.[CH3:18][CH:19]([CH3:24])[CH2:20][CH2:21][Mg]Cl>C1COCC1>[CH3:18][C:19]([CH3:24])([CH2:20][CH3:21])[C:3](=[O:5])[C:2]([N:7]1[CH2:11][CH2:10][CH2:9][CH:8]1[C:12](=[O:17])[CH2:13][CH2:14][CH:15]=[CH2:16])=[O:1]

Participants

4

Reactant 2

HCID 22257821HCID 22257821, compoundHCID 178445868HCID 178445868, compound

Product 1

HCID 22257788HCID 22257788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-oxo-2-(2-pent-4-enoylpyrrolidinyl)acetate (21.0 g; 88 mmol) in 150 ml THF was cooled to −78° C., under nitrogen, and treated with 200 ml (180 mmol) of 0.9 M 3,3-dimethylpropyl magnesium chloride. After stirring for 2.5 hours, TLC indicated that the reaction was complete. It was quenched with 300 ml of saturated NH4Cl followed by 200 ml of ethyl acetate. The layers were separated and the aqueous layer was extracted once more with 300 ml of ethyl acetate. The combined organic layers were dried over MgSO4, filtered, concentrated, and the product purified on silica gel with 20% ethyl acetate in hexane, to obtain 3,3-dimethyl-1-(2-pent-4-enoylpyrrolidinyl)pentane-1,2-dione as a light yellow oil, 21.0 g (85%).

Workup

  1. customIt was quenched with 300 ml of saturated NH4Cl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted once more with 300 ml of ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe product purified on silica gel with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7e8a8321c2e94b479f5f56f0d6a53f9a
Source dataset
uspto-grants-2001_04
Patent number
US06218424B1

Reaction notes

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