Pyridine → t-butyl pyruvate

HRID 2410082Notes

Reaction equation

HRID 2410082 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[C:6](O)(=[O:10])[C:7]([CH3:9])=[O:8].N1C=CC=CC=1.COC(Cl)Cl>C(Cl)Cl>[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:10])[C:7]([CH3:9])=[O:8]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1060Pyruvic AcidHCID 6386tert-ButanolHCID 21004Methane, dichloromethoxy-

Product 1

HCID 11309579t-butyl pyruvate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl pyruvate was prepared as follows: tert-butyl alcohol (444 mg, 6 mmol) and pyruvic acid (528 mg, 6 mmol) were dissolved in methylene chloride (30 mL) and cooled on an ice bath. Pyridine (948 mg. 0.97 mL, 12 mmol) was added, followed by addition of 1,1-dichloromethyl methyl ether (690 mg, 0.53 mL, 6 mmol). The reaction mixture was stirred for 1 h on an ice bath, warmed to room temperature and washed with 30 mL of 5% aqueous HCl, 30 mL of saturated aqueous NaHCO3, and 30 mL of saturated aqueous NaCl. The organic layer was dried over anhydrous MgSO4, filtered and solvent removed on a rotary evaporator to give tert-butyl pyruvate in quantitative yield, slightly contaminated with methylene chloride (as 1H NMR). Aliquots used for biological analyses were cleared of methylene chloride by short path vacuum distillation.

Workup

  1. customtert-Butyl pyruvate was prepared
  2. temperaturecooled on an ice bath
  3. washwashed with 30 mL of 5% aqueous HCl, 30 mL of saturated aqueous NaHCO3, and 30 mL of saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customsolvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-0aa8d3b708b944d098cd1a23ff0d8a3a
Source dataset
uspto-grants-2014_08
Patent number
US08815946B2

Reaction notes

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