Water → Tert-butyl Methyl Oxalate

HRID 876752Notes

Reaction equation

HRID 876752 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].N1C=CC=CC=1.O>CC(OC)(C)C>[CH3:6][O:5][C:3](=[O:4])[C:2]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6386tert-ButanolHCID 79846Methyl chloroglyoxylate

Product 1

HCID 11412538Tert-butyl Methyl Oxalate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of methyl chlorooxoacetate in TBME (1 mmol/ml) was added at 0-5° C. tert-butanol (1.5 equiv.), followed by dropwise addition of pyridine (1.5 equiv.). The resulting mixture was stirred at room temperature for 20 h. Water (15 vol.) was added, the mixture was extracted with TBME twice. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum to give a colorless oil.

Workup

  1. extractionthe mixture was extracted with TBME twice
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under vacuum
  5. customto give a colorless oil

Sources & evidence

ORD record
ord-2668a3a54fc34106af3cc6aa760da276
Source dataset
uspto-grants-2015_03
Patent number
US08987272B2

Reaction notes

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