Carbon Tetrachloride → Tert-butyl 3-cyclopropyl-3-oxopropanoate magnesium salt

HRID 610751Notes

Reaction equation

HRID 610751 reaction equation
[Mg:1].C(Cl)(Cl)(Cl)Cl.[CH:7]1([C:10](=[O:19])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH2:8]1>CO>[Mg:1].[CH:7]1([C:10](=[O:19])[CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 5462224MagnesiumHCID 11126948Tert-butyl 3-cyclopropyl-3-oxopropanoate

Product 1

HCID 70126758Tert-butyl 3-cyclopropyl-3-oxopropanoate magnesium saltYield 132.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Magnesium (3.0 g) was stirred in methanol, carbon tetrachloride (0.5 ml) added and the mixture warmed at 50° C. until the metal had dissolved (1.5 hours). Tert-butyl 3-cyclopropyl-3-oxopropanoate (20.0 g) was then added dropwise and the mixture heated under reflux conditions for 1 hour. The solvent was evaporated and re-evaporated after addition of toluene to give tert-butyl 3-cyclopropyl-3-oxopropanoate magnesium salt (29.9 g) as a white solid, m.p.>300° C., IR max (C=O) 1520, 1540; (C--O) 1350 cm-1.

Workup

  1. dissolutionhad dissolved (1.5 hours)
  2. temperaturethe mixture heated under reflux conditions for 1 hour
  3. customThe solvent was evaporated
  4. customre-evaporated
  5. additionafter addition of toluene

Sources & evidence

ORD record
ord-a64d29862f2f4bd992521c0d85636ce0
Source dataset
uspto-grants-1999_12
Patent number
US05998653

Reaction notes

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