Diethyl acetonedicarboxylate → HCID 533969, compound

HRID 2108315Notes

Reaction equation

HRID 2108315 reaction equation
O=[C:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)(O)[O-].[Na+].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1(C)C=CC=CC=1>[S:29]=[C:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 66045Diethyl acetonedicarboxylateHCID 87949Lawesson's reagentHCID 516892Sodium Bicarbonate

Product 1

HCID 533969HCID 533969, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolve 14.1 mmol of diethyl 3-oxopentanedioate in 15 mL of toluene under argon add 49.4 mmol of sodium bicarbonate and 15.1 mmol of Lawesson's reagent. Stir for 1 h at room temperature then heat under reflux for 5 h. Cool, filter, and concentrate in vacuo. Purify the residue by silica gel chromatography using ethyl acetate/hexanes eluant to yield the title compound.

Workup

  1. temperaturethen heat
  2. temperatureunder reflux for 5 h
  3. temperatureCool
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by silica gel chromatography

Sources & evidence

ORD record
ord-785bf6da1b014f6d91aa47772a600156
Source dataset
uspto-grants-2009_04
Patent number
US07514068B2

Reaction notes

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