Hydrochloric Acid → HCID 15496136, compound

HRID 2358467Notes

Reaction equation

HRID 2358467 reaction equation
[O:1]=[C:2]([CH3:11])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Cl-].[Mg+2].[Cl-].[C:15](Cl)(=[O:17])[CH3:16].Cl>ClCCl.N1C=CC=CC=1>[C:2]([CH:3]([C:15](=[O:17])[CH3:16])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])(=[O:1])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 15538Tert-butyl acetoacetateHCID 5360315Magnesium Chloride

Product 1

HCID 15496136HCID 15496136, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

34.2 ml (0.21 mol) of tert-butyl 3-oxobutanoate were dissolved in 300 ml of dichloromethane, and 20 g (0.21 mol, 1.0 eq.) of anhydrous magnesium chloride were added. At 0° C., 33.9 ml (0.42 mol, 2.0 eq.) of dry pyridine were added to the suspension, which was stirred vigorously. After 15 minutes, 14.3 ml (0.21 mol, 1.0 eq.) of acetyl chloride were added dropwise, and the mixture was stirred at RT for 1 hour. At 0° C., excess pyridine was neutralized with dilute hydrochloric acid (37 ml of conc. hydrochloric acid and 100 ml of water), and the organic phase was separated off. The aqueous phase was extracted with MTBE (3×100 ml), and the combined organic phases were washed with saturated NaCl solution and dried over MgSO4. Removal of the solvent gave 41.2 g (0.206 mol, 98%) of tert-butyl 2-acetyl-3-oxobutanoate in the form of a pale yellow oil.

Workup

  1. stirringthe mixture was stirred at RT for 1 hour
  2. customAt 0° C.
  3. customthe organic phase was separated off
  4. extractionThe aqueous phase was extracted with MTBE (3×100 ml)
  5. washthe combined organic phases were washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-8aa6741945a549f7833eb29cd5ee9247
Source dataset
uspto-grants-2010_07
Patent number
US07763740B2

Reaction notes

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