Ammonium Chloride → 2-Cyclohexyl-2-hydroxy-2-thien-2-ylacetic Acid Methyl Ester

HRID 1244459Notes

Reaction equation

HRID 1244459 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][O:10][C:11](=[O:19])[C:12](=[O:18])[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.[Cl-].[NH4+]>C(OCC)C.C1COCC1>[CH3:9][O:10][C:11](=[O:19])[C:12]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([OH:18])[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 11217486Methyl alpha-oxo-2-thiopheneacetateHCID 178478990HCID 178478990, compound

Product 1

HCID 669594652-Cyclohexyl-2-hydroxy-2-thien-2-ylacetic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

98.6 ml (0.197 mol) of a 2M solution of Cyclohexylmagnesium chloride in diethyl ether, were added to a solution of 27.97 g (0.164 mol) of 2-oxo-2-thien-2-ylacetic acid methyl ester dissolved in 370 ml of THF, at −78° C. under a N2 atmosphere. The mixture was stirred at this temperature for 10 minutes, and then warmed to room temperature. After 1 h, the reaction mixture was treated with a saturated solution of ammonium chloride and extracted three times with ethyl acetate. The organic phases were combined, washed with water, and dried over MgSO4. After removal of the solvent, the oil obtained was purified by column chromatography (silica gel) using hexane/AcOEt 90:10 as eluent. The yield was 16.2 g (39.5%) of a pure product, whose structure was confirmed by 1H-NMR.

Workup

  1. waitAfter 1 h
  2. extractionextracted three times with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent
  6. customthe oil obtained
  7. customwas purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-724a38349dea4c9e9a7ca8e0652fda8d
Source dataset
uspto-grants-2006_10
Patent number
US07122558B2

Reaction notes

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