Dimethyl oxalate → Dimethyl 2-(benzyloxy)-3-oxosuccinate

HRID 2426255Notes

Reaction equation

HRID 2426255 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:14](OC)(=[O:19])[C:15]([O:17][CH3:18])=[O:16].[Li+].CC([N-]C(C)C)C>C1COCC1>[CH2:6]([O:5][CH:4]([C:14](=[O:19])[C:15]([O:17][CH3:18])=[O:16])[C:3]([O:2][CH3:1])=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11120Dimethyl oxalateHCID 2724682Lithium diisopropylamideHCID 11745225Methyl 2-(benzyloxy)acetate

Product 1

HCID 59771073Dimethyl 2-(benzyloxy)-3-oxosuccinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl(benzyloxy)acetate (1 eq) and dimethyl oxalate (1.2 eq) in dry THF was cooled to −78° C. and LDA (2M in THF-heptane, 1.2 eq) was added dropwise. After stirring for an hour the cold bath was removed, and stirring was continued for an additional hour. The reaction was quenched at 0° C. by pouring into cold 1N aq HCl, and the aqueous phase was extracted with EtOAc; the organic layer was washed with brine, dried and concentrated to give a crude that was used without further purification.

Workup

  1. customwas removed
  2. stirringstirring
  3. waitwas continued for an additional hour
  4. customThe reaction was quenched at 0° C.
  5. additionby pouring into cold 1N aq HCl
  6. extractionthe aqueous phase was extracted with EtOAc
  7. washthe organic layer was washed with brine
  8. customdried
  9. concentrationconcentrated
  10. customto give a crude that
  11. customwas used without further purification

Sources & evidence

ORD record
ord-4a0e9e3771e04e76ad5a90ba759c7c0f
Source dataset
uspto-grants-2011_06
Patent number
US07968553B2

Reaction notes

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