Water → HCID 66817034, compound

HRID 1755067Notes

Reaction equation

HRID 1755067 reaction equation
[CH3:1][Mg]Br.[CH2:4]([O:11][C:12]([CH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH:21]=[O:22])[CH2:16][CH2:15]1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>C1COCC1>[CH2:4]([O:11][C:12]([CH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH:21]([OH:22])[CH3:1])[CH2:16][CH2:15]1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 86672780HCID 86672780, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 66817034HCID 66817034, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (1 M solution in THF, 0.526 ml, 0.526 mmol) was added dropwise to 4-(2-oxo-ethyl)-cyclohexanecarboxylic acid benzyl ester (114 mg, 0.439 mmol) in THF (2.2 mL) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. Water was added to the reaction mixture at the same temperature and extracted with ethyl acetate. The organic layer was sequentially washed with a saturated aqueous ammonium chloride solution, water and saturated brine and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 4-(2-hydroxy-propyl)-cyclohexanecarboxylic acid benzyl ester (80.7 mg, 67%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was sequentially washed with a saturated aqueous ammonium chloride solution, water and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ce334521820046e8b81520329e0af556
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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