Ethyl isobutyrate → HCID 68379075, compound

HRID 2172712Notes

Reaction equation

HRID 2172712 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]([O:14][CH2:15][CH3:16])(=[O:13])[CH:10]([CH3:12])[CH3:11].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Cl>O1CCCC1>[CH2:15]([O:14][C:9](=[O:13])[C:10]([CH3:12])([CH3:11])[CH2:22][C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([O:18][CH3:17])[CH:20]=1)[CH3:16]

Participants

5

Reactant 3

HCID 7342Ethyl isobutyrateHCID 699943-Methoxybenzyl chlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 68379075HCID 68379075, compoundYield 106.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium diisopropylamide (2 M in tetrahydrofuran, 2.71 mL, 5.42 mmol) was added to a mixture of ethyl isobutyrate (600 mg, 5.17 mmol) in tetrahydrofuran (60 mL) at −78° C. and stirred at this temperature for 1 hour. 3-Methoxybenzyl chloride (1.15 g, 7.34 mmol) was added dropwise and the reaction mixture was stirred at −78° C. for another 1 hour and then at room temperature overnight. The mixture was quenched by water and extracted with ethyl acetate. The combined organic fractions were washed with water, dried over sodium sulfate and concentrated under vacuum to give ethyl-3-(3-methoxyphenyl)-2,2-dimethylpropanoate (1.3 g) as a yellow oil, which was used in the next step without further purification.

Workup

  1. stirringthe reaction mixture was stirred at −78° C. for another 1 hour
  2. customat room temperature
  3. customovernight
  4. customThe mixture was quenched by water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic fractions were washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-671ba5740c35401fb7f7df5bd95f4fd1
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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