Methyl iodide → 4-(Tert-butoxy)-3-methyl-4-oxobutanoic acid

HRID 2384077Notes

Reaction equation

HRID 2384077 reaction equation
[Li+].[CH3:2]C([N-]C(C)C)C.[C:9]([O:13][C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])([CH3:12])([CH3:11])[CH3:10].CI>C1COCC1>[C:9]([O:13][C:14](=[O:20])[CH:15]([CH3:2])[CH2:16][C:17]([OH:19])=[O:18])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 41391074-(Tert-butoxy)-4-oxobutanoic acid

Product 1

HCID 127614644-(Tert-butoxy)-3-methyl-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of LDA (6.3 mmol, 2M in hexane) in THF (5 mL) at −78° C. is added a solution of succinic acid mono-tert-butyl ester (523 mg, 3 mmol) in THF (2 mL) dropwise. After the addition, the mixture is warmed to −20° C. slowly and stirred at −20° C. for 30 minutes. The solution is re-cooled to −78° C. and MeI (511 mg, 3.6 mmol) is added dropwise. The mixture is warmed to room temperature and stirred for 18 hours. The mixture is quenched with water and extracted with ethyl acetate. The organic layer is washed with water, brine, dried over MgSO4 and filtered. The solvent is removed under reduced pressure to give 2-methyl-succinic acid 1-tert-butyl ester.

Workup

  1. additionAfter the addition
  2. temperatureThe solution is re-cooled to −78° C.
  3. temperatureThe mixture is warmed to room temperature
  4. stirringstirred for 18 hours
  5. customThe mixture is quenched with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer is washed with water, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e790142049e341c49e715f78b7845cef
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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