Methanol → (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

HRID 547099Notes

Reaction equation

HRID 547099 reaction equation
C[Si](C=[N+]=[N-])(C)C.[CH3:8]CCCCC.[Cl:14][C:15]1[CH:16]=[C:17]([C@@H:21]([OH:25])[C:22]([OH:24])=[O:23])[CH:18]=[CH:19][CH:20]=1.CO>C1C=CC=CC=1>[CH3:8][O:23][C:22](=[O:24])[C@@H:21]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[CH:16]=1)[OH:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

Product 1

HCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetateYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of trimethylsilyldiazomethane in hexane (2 M, 1.5 mL, 3.0 mmol) was added to a solution of (R)-(3-chloro-phenyl)hydroxy-acetic acid (497 mg, 2.66 mmol) in benzene (2.6 mL)-methanol (1.3 mL) under cooling with ice. Then, the ice bath was removed and the mixture was stirred at room temperature for five minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to give the title compound (533 mg, 100%).

Workup

  1. temperatureunder cooling with ice
  2. customThen, the ice bath was removed
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-acb4e590f4b54af78e766fdbdfa59cb8
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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