Acetone → HCID 19813064, compound

HRID 467032Notes

Reaction equation

HRID 467032 reaction equation
CO[C:3]1[C:4]([CH2:8][C:9]([OH:11])=[O:10])=[CH:5][S:6][CH:7]=1.[C:12](=O)([O-])[O-:13].[K+].[K+].CI.Cl.[CH3:21][C:22]([CH3:24])=O>>[CH3:12][O:13][C:21]1[CH:22]=[CH:24][C:4]([CH2:8][C:9]([OH:11])=[O:10])=[CH:3][C:7]=1[S:6][CH3:5]

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19813065HCID 19813065, compound

Product 1

HCID 19813064HCID 19813064, compoundYield 96%

Procedure

To a suspension of 4-methoxy-3-thiophenylacetic acid (1.61 g, 81 mmol) in acetone was added potassium carbonate (56 g, 400 mmol, 5 equivalents), followed by methyl iodide (11.5 g, 81 mmol, 1 equivalent). After stirring at ambient temperature for 5.5 hours, 2N aqueous hydrochloric acid solution (400 mL) was slowly added. The resulting solution was then extracted with 2×200 mL of THF/diethyl ether (1:1) followed by diethyl ether (400 mL). The combined organic layers were washed with 2×250 mL of 10% aqueous sodium thiosulfate and 250 mL of saturated aqueous sodium chloride solution (brine), dried over anhydrous magnesium sulfate, filtered and concentrated to give 56 g (96% yield) of the title compound as a pale yellow solid; DCI MS M/Z: 230 (M+NH4)+ ; 1H NMR (CD3OD) δ 3.36 (s, 3H), 3.53 (s, 2H), 3.82 (s, 3H), 6.83 (d, 1H, J=8.7 Hz), 7.02 (dd, 1H, J=8.7, 2.7 Hz), 7.06 (d, 1H, J=2.7 Hz).

Workup

  1. extractionThe resulting solution was then extracted with 2×200 mL of THF/diethyl ether (1:1)
  2. washThe combined organic layers were washed with 2×250 mL of 10% aqueous sodium thiosulfate and 250 mL of saturated aqueous sodium chloride solution (brine)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-05aaa375da3646568fd1e4e4bbe15022
Source dataset
uspto-grants-1992_10
Patent number
US05158948

Reaction notes

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