Methanol → Methyl 3-(methylsulfinyl)benzeneacetate

HRID 391593Notes

Reaction equation

HRID 391593 reaction equation
[CH3:1][S:2]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)=[O:3].[C:14](N1C=CN=C1)(N1C=CN=C1)=O.CO>C1COCC1>[CH3:1][S:2]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 45925729[3-(Methanesulfinyl)phenyl]acetic acid

Product 1

HCID 57657981Methyl 3-(methylsulfinyl)benzeneacetateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [3-(methylsulfinyl)phenyl]acetic acid (1.31 g, 6.60 mmol) and carbonyldiimidazole (1.18 g, 7.26 mmol) in 25.0 mL THF was stirred at room temperature for 15 minutes, then methanol (2.1 mL, 52.8 mmol) was added. After 10 minutes the reaction was briefly warmed to near reflux temperature, then allowed to cool to room temperature. After 20 minutes, the reaction was partitioned between EtOAc and NaHCO3/brine mixture. The EtOAc layer was washed with dilute brine, dilute HCl solution, brine, dried with anhydrous Na2SO4 and rotary evaporated to give the title compound as a yellow-orange oil (1.14 g, 82%).

Workup

  1. temperatureAfter 10 minutes the reaction was briefly warmed
  2. temperatureto near reflux temperature
  3. customthe reaction was partitioned between EtOAc and NaHCO3/brine mixture
  4. washThe EtOAc layer was washed with dilute brine, dilute HCl solution, brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customrotary evaporated

Sources & evidence

ORD record
ord-0f66d3f445d8412babd707ed7071c278
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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