Diethyl Oxalate → HCID 57443248, compound

HRID 2261731Notes

Reaction equation

HRID 2261731 reaction equation
[Mg].Br[CH2:3][CH:4]1[CH2:7][CH2:6][CH2:5]1.[C:8](OCC)(=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C1COCC1>[CH2:12]([O:11][C:9](=[O:10])[C:8](=[O:14])[CH2:3][CH:4]1[CH2:7][CH2:6][CH2:5]1)[CH3:13]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 2734658(Bromomethyl)cyclobutaneHCID 5462224Magnesium

Product 1

HCID 57443248HCID 57443248, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of 5 mg per mL Rieke® magnesium in THF (37.9 mmol, 40 mL) at room temperature is added bromomethyl cyclobutane (37.9 mmol, 4.25 mL) dropwise. After the addition, the reaction is heated to 60° C. for 1 h. The mixture is transferred via syringe to a −78° C. solution of diethyl oxalate (37.9 mmol, 5.14 g) in THF (20 mL). The reaction is allowed to warm to 0° C. and is quenched with 1N HCl. Diethyl ether is added (20 mL) and the layers are separated. The organic layer is dried (Na2SO4) and adsorbed onto silica and purified using a gradient to 0-10% EtOAc/Hexanes to yield the title compound (2.3 g, 37%). LC-MS: 171.0 (M+1).

Workup

  1. additionAfter the addition
  2. customThe mixture is transferred via syringe to a −78° C.
  3. temperatureto warm to 0° C.
  4. customis quenched with 1N HCl
  5. additionDiethyl ether is added (20 mL)
  6. customthe layers are separated
  7. dry with materialThe organic layer is dried (Na2SO4)
  8. custompurified

Sources & evidence

ORD record
ord-b563ed669b7945f49bf1e8f442d94dc8
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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