Diethyl Oxalate → HCID 57444092, compound

HRID 875098Notes

Reaction equation

HRID 875098 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:11])[CH2:5][CH2:6][C:7]([CH3:10])([CH3:9])[CH:8]=1.[C:12](OCC)(=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C(OCC)C.O1CCCC1>[CH3:1][O:2][C:3]1[C:4](=[O:11])[CH:5]([C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][C:7]([CH3:9])([CH3:10])[CH:8]=1

Participants

6

Reactant 3

HCID 7268Diethyl OxalateHCID 586875HCID 586875, compoundHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 57444092HCID 57444092, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methoxy-4,4-dimethyl-cyclohex-2-enone (12.5 g, 81.1 mmol) and diethyl oxalate (12.1 mL, 89.2 mmol) in ethyl ether was treated with a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran under argon atmosphere. The reaction was stirred at room temperature for 2 hours, poured into a 10% NaH2PO4 solution (500 mL) and extracted with diethyl ether (300 mL×2). The organic extracts were washed with brine, dried on Na2SO4 and evaporated to dryness. The crude material was taken up with hexane, stirred and filtered to give the title compound (16.8 g, 81.5% yield) as a yellow crystalline solid.

Workup

  1. extractionextracted with diethyl ether (300 mL×2)
  2. washThe organic extracts were washed with brine
  3. customdried on Na2SO4
  4. customevaporated to dryness
  5. stirringstirred
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c5dcc4d3720f4bee8ce1fc6d089b9724
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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