Ammonium Chloride → 2-Cyclopentyl-2-hydroxy-4-methyl-4-phenylpentanoic Acid-ethyl Ester

HRID 1292974Notes

Reaction equation

HRID 1292974 reaction equation
[CH:1]1([Mg]Cl)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([O:10][C:11](=[O:24])[C:12](=[O:23])[CH2:13][C:14]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[CH3:9].[NH4+].[Cl-]>C1COCC1>[CH2:8]([O:10][C:11](=[O:24])[C:12]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([OH:23])[CH2:13][C:14]([CH3:15])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:22])[CH3:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 113337794-Methyl-2-oxo-4-phenylpentanoic acid ethyl esterHCID 178478989HCID 178478989, compound

Product 1

HCID 694206862-Cyclopentyl-2-hydroxy-4-methyl-4-phenylpentanoic Acid-ethyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.13 ml of a 2 M ethereal cyclopentyl magnesium chloride solution is added in drops at −70° C. to a solution of 1.0 g of 4-methyl-4-phenyl-2-oxopentanoic acid-ethyl ester in 20 ml of THF. After 3 hours at −70° C., the batch is poured into cold, saturated NH4Cl solution and extracted with ethyl acetate. The extracts are dried (Na2SO4) and concentrated by evaporation. Column chromatography on silica gel with ethyl acetate-cyclohexane yields 320 mg of the product.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts are dried (Na2SO4)
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9382b52579c244e18a8cd579d78d25a7
Source dataset
uspto-grants-2007_07
Patent number
US07238707B2

Reaction notes

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