Hydrochloric Acid → Ethyl 3-methyl-2-oxobutyrate

HRID 2185680Notes

Reaction equation

HRID 2185680 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[C:6]([O:13][CH2:14][CH3:15])(=[O:12])[C:7]([O:9]CC)=O.Cl>C(OCC)C>[O:9]=[C:7]([CH:1]([CH3:3])[CH3:2])[C:6]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 178418918HCID 178418918, compound

Product 1

HCID 88406Ethyl 3-methyl-2-oxobutyrate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

Isopropylmagnesium chloride (2.0M in ether, 200 mmol) was added to a solution of diethyl oxalate (29.23 g, 20.0 mmol) in dry diethyl ether (100 ml) at −70° C. over a period of one hour. The mixture was stirred at −70° C. for a further half an hour and then poured immediately into a vigorously stirred suspension of ice (80 g), diethyl ether (100 ml) and concentrated HCl (18 ml). The aqueous phase was separated out and the organic phase washed with water (100 ml) and then dried (MgSO4) and the solvent was removed in order to leave the desired product in the form of a colourless oil.

Workup

  1. customThe aqueous phase was separated out
  2. washthe organic phase washed with water (100 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed in order

Sources & evidence

ORD record
ord-445445343a0149c5b138ecdc0ae48ecb
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

Loading…