Sodium hydride → HCID 18755517, compound

HRID 1838643Notes

Reaction equation

HRID 1838643 reaction equation
[C:1]([C:4]1([CH2:7][CH2:8][C:9]([O:11]C)=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+]>O1CCCC1.CN(C)C=O>[CH2:5]1[C:4]2([CH2:7][CH2:8][C:9](=[O:11])[CH2:2][C:1]2=[O:3])[CH2:6]1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 18755522HCID 18755522, compound

Product 1

HCID 18755517HCID 18755517, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

74.5 g of methyl 3-(1-acetylcyclopropyl)propionate (0.32 mol) are dissolved in 1 l of tetrahydrofuran and the solution is treated portionwise with 14.3 g of sodium hydride (55% suspension in oil, 0.32 mol) at room temperature. After 1 hour, the reaction mixture is diluted with 200 ml of dimethylformamide and warmed to 70° C. After 8 hours, tetrahydrofuran is removed in vacuo, and the residue is poured into 2 N hydrochloric acid and extracted with diethyl ether. The organic phase is dried over sodium sulfate and concentrated, and column chromatography over silica gel (methylene chloride:ethanol 9:1 as eluent) gives spiro[2.5]octane-4,6-dione in the form of white crystals of melting point 116-118° C.

Workup

  1. waitAfter 8 hours
  2. customtetrahydrofuran is removed in vacuo
  3. additionthe residue is poured into 2 N hydrochloric acid
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-66259813c312410cafe0acbea40192b4
Source dataset
uspto-grants-2004_01
Patent number
US06673938B1

Reaction notes

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