Diethyl Oxalate → HCID 66770448, compound

HRID 401677Notes

Reaction equation

HRID 401677 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[C:19]([CH3:24])[C:20](=[O:23])[CH2:21][CH3:22])=[CH:14][CH:13]=1.[C:25]([O:32][CH2:33][CH3:34])(=[O:31])[C:26]([O:28]CC)=O>C1COCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]=[C:19]([CH3:24])[C:20](=[O:23])[CH:21]([CH3:22])[C:26](=[O:28])[C:25]([O:32][CH2:33][CH3:34])=[O:31])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 2733832Lithium HexamethyldisilazideHCID 66840740HCID 66840740, compound

Product 1

HCID 66770448HCID 66770448, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of LiHMDS (1N solution in THF, 5.48 mmol, 5.17 mL) in THF (16 mL) at −78° C. was added a solution of 46b (4.98 mmol, 1.04 g) in THF (2.5 mL) drop wise. After stirring at −78° C. for 1 h, the mixture was treated with a solution of diethyl oxalate (4.98 mmol, 0.73 g) in THF (2.5 mL). After stirring at −78° C. for 1 h, then the mixture was warmed up to room temperature and stirred overnight. The solvent was evaporated and the crude product was taken up in EtOAc, and washed with 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated to give 1.5 g of 46c.

Workup

  1. stirringAfter stirring at −78° C. for 1 h
  2. temperaturethe mixture was warmed up to room temperature
  3. stirringstirred overnight
  4. customThe solvent was evaporated
  5. washwashed with 1N HCl and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9a5d6657a7a3481eb40b84a00977165e
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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