Potassium Carbonate → 4-Methyl-2-oxo-4-phenylpentanoic acid ethyl ester

HRID 1292973Notes

Reaction equation

HRID 1292973 reaction equation
[C:1]1([C:7](O)([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([O:13][C:14](=[O:22])[C:15]([O:17][Si](C)(C)C)=[CH2:16])[CH3:12].[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:11]([O:13][C:14](=[O:22])[C:15](=[O:16])[CH2:17][C:7]([CH3:9])([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])[CH3:12]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 120532-Phenyl-2-propanolHCID 24287Tin tetrachlorideHCID 111168062-Trimethylsilanyloxy-acrylic acid ethyl ester

Product 1

HCID 113337794-Methyl-2-oxo-4-phenylpentanoic acid ethyl esterYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 g of 2-phenyl-2-propanol and 30.4 g of 2-(trimethylsilyloxy)acrylic acid-ethyl ester (Bull. Chem. Soc. Jpn. 1992, 65, 3209) are introduced into 386 ml of CH2Cl2 and treated at −70° C. with 11.5 ml of tin tetrachloride. After 15 minutes at −70° C., the batch is introduced into semiconcentrated potassium carbonate solution, extracted with CH2Cl2, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with ethyl acetate-cyclohexane yields 4.64 g of the product as a colorless oil.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-9acc1559ef844573809699b8d495c4cf
Source dataset
uspto-grants-2007_07
Patent number
US07238707B2

Reaction notes

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